Dimethylformamide → (S)-tert-Butyl 3-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate

HRID 418520Notes

Reaction equation

HRID 418520 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]1)[C:7]2=[O:13].[F:26][C:27]1[CH:28]=[C:29]([CH2:37][C:38](O)=[O:39])[CH:30]=[CH:31][C:32]=1[C:33]([F:36])([F:35])[F:34].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CN(C)C=O>>[F:26][C:27]1[CH:28]=[C:29]([CH2:37][C:38]([NH:1][C:2]2[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]([C@H:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]2)[C:7]3=[O:13])=[O:39])[CH:30]=[CH:31][C:32]=1[C:33]([F:35])([F:36])[F:34]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27375913-Fluoro-4-(trifluoromethyl)phenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66649434(S)-tert-butyl 3-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate

Product 1

HCID 66649399(S)-tert-Butyl 3-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate

Conditions

Temperature
45 °C

Procedure

A reaction vial was charged with (S)-tert-butyl 3-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate (150.00 mg, 0.043678 mmol), 2-(3-fluoro-4-(trifluoromethyl)phenyl)acetic acid (116.4 mg, 0.05241 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (420 mg, 1.1 mmol), N,N-diisopropylethylamine (0.19 mL, 1.1 mmol) and N,N-dimethylformamide (2 mL, 20 mmol) and the reaction was stirred at 45° C. overnight. The solvent was removed under reduced pressure and the residue purified by flash chromatography to afford the product as light yellow oil.

Workup

  1. customA reaction
  2. customThe solvent was removed under reduced pressure
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-ac73c5bfa2c94d85bf27df09fcf15ede
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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