Methylamine hydrochloride → HCID 11691383, compound

HRID 1027934Notes

Reaction equation

HRID 1027934 reaction equation
[Cl:1][C:2]1[C:3]([F:32])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:30][CH3:31])=[C:16]([O:19][C@H:20]4[CH2:25][CH2:24][N:23]([CH3:26])[C@@H:22]([C:27](O)=[O:28])[CH2:21]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:34][NH2:35]>>[Cl:1][C:2]1[C:3]([F:32])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:30][CH3:31])=[C:16]([O:19][C@H:20]4[CH2:25][CH2:24][N:23]([CH3:26])[C@@H:22]([C:27]([NH:35][CH3:34])=[O:28])[CH2:21]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6364545Methylamine hydrochlorideHCID 58318656HCID 58318656, compound

Product 1

HCID 11691383HCID 11691383, compound

Procedure

(2R,4S)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)-1-methylpiperidine-2-carboxylic acid (20) was coupled with methylamine hydrochloride analogously as for the equivalent step in Example 7 to give the title compound (2R,4S)-4-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)-N,1-dimethylpiperidine-2-carboxamide: 1H NMR Spectrum: (DMSO-d6) δ1.63-1.72 (2H, m), 2.15-2.21 (6H, m), 2.55-2.62 (4H, m), 2.93-2.98 (1H, m), 3.94 (3H, s), 4.43-4.51 (1H, m), 7.23 (1H, s), 7.28-7.33 (1H, m), 7.49-7.56 (2H, m), 7.68-7.72 (1H, m), 7.86 (1H, s), 8.39 (1H, s), 9.57 (1H, s); Mass Spectrum: (M+H)+ 474.

Sources & evidence

ORD record
ord-71fa9d4b262e48f7ae80fd18ed753ae5
Source dataset
uspto-grants-2014_05
Patent number
US08735410B2

Reaction notes

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