Dimethylformamide → N-(2-(2-Amino-2-oxoethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-chloro-3-(trifluoromethyl)phenyl)acetamide

HRID 1161207Notes

Reaction equation

HRID 1161207 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].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.[NH2:54][C:55]1[CH:64]=[CH:63][CH:62]=[C:61]2[C:56]=1[CH:57]=[CH:58][N:59]([CH2:66][C:67]([NH2:69])=[O:68])[C:60]2=[O:65]>>[NH2:69][C:67](=[O:68])[CH2:66][N:59]1[CH:58]=[CH:57][C:56]2[C:61](=[CH:62][CH:63]=[CH:64][C:55]=2[NH:54][C:9](=[O:11])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:12]([F:15])([F:14])[F:13])[CH:4]=2)[C:60]1=[O:65]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 35198824-Chloro-3-(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 595159242-(5-Amino-1-oxoisoquinolin-2(1H)-yl)acetamide

Product 1

HCID 24760010N-(2-(2-Amino-2-oxoethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-chloro-3-(trifluoromethyl)phenyl)acetamide

Procedure

A round bottom flask was charged with 2-(4-chloro-3-(trifluoromethyl)phenyl)acetic acid (170 mg, 0.00072 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (400 mg, 0.001 mol), N,N-diisopropylethylamine (0.2 mL, 0.001 mol), N,N-dimethylformamide (2 mL, 0.03 mol) and 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)acetamide (120 mg, 0.00055 mol). The reaction was stirred for 16 h at room temperature and the solvent was removed and the residue purified by preparative HPLC (reverse phase) to yield the product as a white powder. MS m/z=437.8 (M+1). 1H NMR (400 MHz; DMSO-d6) δ 10.09 (s, 1H), 8.04 (d, J=8.07 Hz, 1H), 7.89 (bs, 1H), 7.83 (d, J=8.07 Hz, 1H), 7.73-7.70 (m, 2H), 7.63 (bs, 1H), 7.46 (t, J=8.0 Hz, 1H), 7.42 (d, J=7.76 Hz, 1H) 7.19 (bs, 1H), 6.64 (d, J=7.70 Hz, 1H), 4.56 (s, 2H), 3.92 (s, 2H).

Workup

  1. customthe solvent was removed
  2. customthe residue purified by preparative HPLC (reverse phase)

Sources & evidence

ORD record
ord-a035f01367f246b7a843cef31b2ddfe3
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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