Category: 27810-64-6

Analyzing the synthesis route of 27810-64-6

27810-64-6, 27810-64-6 Isoquinoline-5-carboxylic acid 260936, aisoquinoline compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.27810-64-6,Isoquinoline-5-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To a stirring solution of corresponding picolinic or nicotinic acids (1.0 eq.), EDCI (1.5 eq.) and HOBt (1.0 eq.)in CH2Cl2 at room temperature was added Et3N (2 eq.) dropwise, followed by the amine. The resultedmixture was stirred for 16 h and afterwards diluted by excess amount of CH2Cl2. The organic solution waswashed by water and dried over Na2SO4. A yellow residue was obtained after concentration and purified byflash column on silica gel to afford compound S2. To a solution of S2 (1.0 eq.) in THF at 78 was addedn-BuLi (1.1 eq.) or LDA (1.1 eq.) dropwise. The resulted mixture was stirred at this temperature for 15 min.A solution of corresponding acryloyl chloride (1.3 eq. while using n-BuLi and 2.5 eq. while using LDA) wasadded dropwise at 78. The reaction was warmed to room temperature gradually and stirred for another5 h . Afterwards, the reaction mixture was diluted with EtOAc and the organic solution was washed bywater and dried over Na2SO4. A brown residue was obtained after concentration and purified by flashcolumn on silica gel to afford the compound 4. Analytical data of 4q and 4r are consistent with the previousreports

27810-64-6, 27810-64-6 Isoquinoline-5-carboxylic acid 260936, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Article; Ma, Jiajia; Strieth-Kalthoff, Felix; Dalton, Toryn; Freitag, Matthias; Schwarz, J. Luca; Bergander, Klaus; Daniliuc, Constantin; Glorius, Frank; Chem; vol. 5; 11; (2019); p. 2854 – 2864;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Simple exploration of 27810-64-6

As the paragraph descriping shows that 27810-64-6 is playing an increasingly important role.

27810-64-6, Isoquinoline-5-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

192A. N-(l-Methylpiperidin-4-yl)isoquinoline-5-carboxamide: To isoquinoline- 5-carboxylic acid (0.22 g, 1.270 mmol) and l-methylpiperidin-4-amine (0.145 g, 1.270 mmol) in EtOAc (3 mL)/DMF(l mL) was added TEA (0.48 mL, 3.464 mmol) and a 50% EtOAc solution of T3P (0.306 mL, 1.082 mmol). After 24h, the reaction was partitioned with water (15 mL) and ethyl acetate (50 mL). The organic layer was washed with brine (10 mL) and dried (MgS04). MS (ESI) m/z: 270.1 (M+H)+., 27810-64-6

As the paragraph descriping shows that 27810-64-6 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; SMITH, II, Leon M.; ORWAT, Michael J.; JEON, Yoon; CORTE, James R.; WO2014/160668; (2014); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Downstream synthetic route of 27810-64-6

The synthetic route of 27810-64-6 has been constantly updated, and we look forward to future research findings.

27810-64-6, Isoquinoline-5-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A round bottom flask was charged with isoquinoline-5-carboxylic acid (50 mg, 0.29 mmol, 1.05 eq) suspended in SOCl2 (2 mL). After addition of 3 drops of DMF the reaction was heated to 70C for 60 min and excess SOCl2 was removed under reduced pressure. The resulting solid was re-dissolved in DCM (3 mL) and after addition of DiPEA (140 muL, 0.41 mmol, 3 eq) a solution of tert-butyl(E)-(2-aminoethyl)(3-(4-(pyridin-3-yl)phenyl) allyl) carbamate (63) (97 mg, 0.275 mmol, 1 eq) and DMAP (3 mg, 0.03 mmol, 0.1 eq) dissolved in DCM (5 mL) was added dropwise at 0C. The reaction mixture was allowed to warm up to RT. After 75 min half saturated aqueous NaHCO3 solution (10 mL) was added, the mixture was extracted with DCM (3×15 mL), the combined organic layers were washed with brine (1×40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified via flash-column-chromatography (SiO2, 0% to 15% MeOH in DCM) to yield the product (57 mg, 41%). 1H NMR (400 MHz, chloroform-d) delta 9.26 (s, 1H), 8.85 (s, 1H), 8.62 – 8.51 (m, 2H), 8.36 – 8.16 (m, 1H), 8.03 (d, J = 8.2 Hz, 1H), 7.88 (d, J = 7.7 Hz, 2H), 7.62 – 7.33 (m, 7H), 6.55 (d, J = 15.9 Hz, 1H), 6.32 – 6.19 (m, 1H), 4.09 (bs, 2H), 3.73 (d, J = 5.3 Hz, 2H), 3.62 (bs, 2H), 1.41 (s, 9H). 13C NMR (101 MHz, chloroform-d) delta 168.47, 157.28, 152.82, 148.61, 148.18, 144.24, 137.20, 136.37, 136.16, 134.26, 133.35, 132.83, 131.68, 130.61, 129.46, 128.84, 127.45, 127.21, 126.24, 125.80, 123.73, 118.58, 80.77, 50.08, 45.59, 40.30, 28.42. LCMS (ESI, Thermo, C18, linear gradient, 10% to 90% ACN in H2O, 0.1% TFA, 10.5 min): tR = 4.67 min; m/z : 509 [M+H]+.

The synthetic route of 27810-64-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Grimm, Sebastian H.; Gagestein, Berend; Keijzer, Jordi F.; Liu, Nora; Wijdeven, Ruud H.; Lenselink, Eelke B.; Tuin, Adriaan W.; van den Nieuwendijk, Adrianus M.C.H.; van Westen, Gerard J.P.; van Boeckel, Constant A.A.; Overkleeft, Herman S.; Neefjes, Jacques; van der Stelt, Mario; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 692 – 699;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem