Dimethylformamide → HCID 25013605, compound

HRID 418492Notes

Reaction equation

[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:15]([CH3:19])[C:16]([NH2:18])=[O:17])[C:7]2=[O:14].[F:20][C:21]([F:33])([F:32])[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=[O:30])=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.CN(C)C=O>>[CH3:13][O:12][C:11]1[C:2]([NH:1][C:29](=[O:30])[CH2:28][C:25]2[CH:24]=[CH:23][C:22]([C:21]([F:32])([F:20])[F:33])=[CH:27][CH:26]=2)=[C:3]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:14])[N:6]([C@H:15]([CH3:19])[C:16]([NH2:18])=[O:17])[CH:5]=[CH:4]2

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid

HCID 59515704HCID 59515704, compound

Product 1

HCID 25013605HCID 25013605, compound

Procedure

A mixture of (R)-2-(5-amino-6-methoxy-1-oxoisoquinolin-2(1H)-yl)propanamide (98.34 mg, 0.0003764 mol), 2-(4-(trifluoromethyl)phenyl)acetic acid (115.2 mg, 0.0005646 mol), N,N-diisopropylethylamine (163.9 μL, 0.0009409 mol), N,N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (357.8 mg, 0.0009409 mol) and N,N-dimethylformamide (2 mL, 0.02 mol) was stirred at room temperature overnight. the solvent was removed under reduced pressure and the residue purified by reverse phase preparative HPLC to afford the product as a light yellow solid.

Workup

customthe solvent was removed under reduced pressure
customthe residue purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-2ce9ede9beef4c61b59a37d9f0e4068e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093265B2

Reaction notes

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