Ammonium Chloride → N2-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-[(1S)-2-methoxy-1-methylethyl]-D-alaninamide

HRID 1867709Notes

Reaction equation

HRID 1867709 reaction equation
[Cl:1][C:2]1[C:3]([F:33])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:31][CH3:32])=[C:16]([CH2:19][N:20]([C@@H:26]([CH3:30])[CH2:27][O:28][CH3:29])[C@@H:21]([C:23]([OH:25])=O)[CH3:22])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+:35]>>[Cl:1][C:2]1[C:3]([F:33])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:31][CH3:32])=[C:16]([CH2:19][N:20]([C@@H:26]([CH3:30])[CH2:27][O:28][CH3:29])[C@@H:21]([C:23]([NH2:35])=[O:25])[CH3:22])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 25517Ammonium ChlorideHCID 57979849N-({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-[(1S)-2-methoxy-1-methylethyl]-D-alanine

Product 1

HCID 57979856N2-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-[(1S)-2-methoxy-1-methylethyl]-D-alaninamide

Procedure

N-({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-[(1S)-2-methoxy-1-methylethyl]-D-alanine was coupled with ammonium chloride using a procedure analogous to the equivalent step in Example 16 to give the title product; 1H NMR Spectrum: (DMSO-d6) 1.07 (d, 3H); 1.24 (d, 3H); 2.99 (m, 1H); 3.18 (m, 4H); 3.47 (m, 2H); 3.83 (d, 1H); 3.89 (d, 1H); 3.97 (s, 3H); 6.98 (m, 1H); 7.21 (s, 1H); 7.30 (dt, 1H); 7.50 (m, 1H); 7.60 (m, 2H); 8.37 (s, 1H); 8.44 (s, 1H); 9.64 (s, 1H); Mass Spectrum: (M+H)+ 476.

Sources & evidence

ORD record
ord-b8a7e157e4884ace85e1c4fdc121b67f
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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