Diisopropylethylamine → HCID 59579304, compound

HRID 1037787Notes

Reaction equation

HRID 1037787 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:14])[C:7]2=[O:12].[F:21][C:22]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:32][C:33](O)=[O: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=O)C>[F:21][C:22]1[C:27]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:32][C:33]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:14])[C:7]2=[O:12])=[O:34]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27375882-Fluoro-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 59579790HCID 59579790, compound

Product 1

HCID 59579304HCID 59579304, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 5-amino-2-(1-(pyridin-2-yl)ethyl)isoquinolin-1(2H)-one (100 mg, 0.0004 mol) in N,N-Dimethylformamide (1 mL, 0.01 mol) was added 2-(2-fluoro-3-(trifluoromethyl)phenyl)acetic acid (178 mg, 0.000801 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (468.3 mg, 0.001232 mol) and N,N-diisopropylethylamine (300 uL, 0.002 mol). The reaction mixture was stirred for 16 hours at 50° C. LC/MS indicated that the reaction was completed. The DMF reaction solution was directly applied to prep. HPLC. The final product was obtained as a solid (102.4 mg). MS m/z=470.3 (M+1). 1H NMR (DMSO) δ 10.17 (s, 1 H), 8.54 (d, J=6.4 Hz, 1 H), 8.10 (d, J=8.0 Hz, 1 H), 7.82 (dd, J=7.8, 0.7 Hz, 1 H), 7.78 (td, J=9.5, 1.8 Hz, 2 H), 7.70 (t, J=7.1 Hz, 1 H), 7.55 (d, J=7.8 Hz, 1 H), 7.48 (t, J=7.9 Hz, 1 H), 7.40 (t, J=7.7 Hz, 1 H), 7.35 (d, J=8.0 Hz, 1 H), 7.31 (qd, J=4.8, 0.9 Hz, 1 H), 6.74 (d, J=7.8 Hz, 1 H), 6.28 (q, J=7.2 Hz, 1 H), 3.98 (s, 2 H), 1.78 (d, J=7.2 Hz, 3 H).

Sources & evidence

ORD record
ord-c6b9b887115e4c2ca2d60a77028a3bdb
Source dataset
uspto-grants-2013_10
Patent number
US08546579B2

Reaction notes

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