7-Amino-1-(2-methoxyethyl)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one → 2-{2-[1-(2-Methoxyethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino]-5-trifluoromethylpyrimidin-4-ylamino]-N-methylbenzamide

HRID 1687491Notes

Reaction equation

HRID 1687491 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=1.[NH2:23][C:24]1[CH:39]=[CH:38][C:27]2[N:28]([CH2:34][CH2:35][O:36][CH3:37])[C:29](=[O:33])[CH2:30][CH2:31][CH2:32][C:26]=2[CH:25]=1>>[CH3:37][O:36][CH2:35][CH2:34][N:28]1[C:29](=[O:33])[CH2:30][CH2:31][CH2:32][C:26]2[CH:25]=[C:24]([NH:23][C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=4[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=3)[CH:39]=[CH:38][C:27]1=2

Participants

3

Reactant 2

HCID 434466107-Amino-1-(2-methoxyethyl)-1,3,4,5-tetrahydrobenzo[b]azepin-2-oneHCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide

Product 1

HCID 668305202-{2-[1-(2-Methoxyethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino]-5-trifluoromethylpyrimidin-4-ylamino]-N-methylbenzamide

Procedure

The title compound was prepared from 2-(2-chloro-5-trifluoromethyl-pyrimidin-4-ylamino)-N-methyl-benzamide and 7-amino-1-(2-methoxyethyl)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one in an analogous manner to Example 195 (microwave: 120° C., 90 minutes) to afford a white solid (29 mg, 47%). Mp: 73-6° C. LCMS (m/e) 529 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 10.90 (s, 1H), 8.44 (d, J=9 Hz, 1H), 8.39 (s, 1H), 7.50-7.40 (m, 4H), 7.24 (m, 1H), 7.15 (m, 2H), 6.20 (br s, 1H), 4.00 (br m, 2H) 3.57 (t, 2H, J=5 Hz), 3.32 (s, 3H), 3.04 (d, J=5 Hz, 3H), 2.67 (br m, 2H), 2.31 (t, J=5 Hz, 2H), 2.13 (br m, 2H).

Sources & evidence

ORD record
ord-30f38238e2fa490da645ba09727be67b
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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