7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one → HCID 67264158, compound

HRID 1687718Notes

Reaction equation

HRID 1687718 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7](=[O:13])[CH2:8][CH2:9][C:10]([CH3:12])([CH3:11])[C:4]=2[CH:3]=1.Cl[C:17]1[N:22]=[C:21]([NH:23][C:24]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:25]=2[C:26]([NH:28][CH2:29][CH3:30])=[O:27])[C:20]([Cl:36])=[CH:19][N:18]=1>>[Cl:36][C:20]1[C:21]([NH:23][C:24]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:25]=2[C:26]([NH:28][CH2:29][CH3:30])=[O:27])=[N:22][C:17]([NH:1][C:2]2[CH:15]=[CH:14][C:5]3[NH:6][C:7](=[O:13])[CH2:8][CH2:9][C:10]([CH3:12])([CH3:11])[C:4]=3[CH:3]=2)=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 578538307-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneHCID 866339272-(2,5-Dichloro-pyrimidin-4-ylamino)-N-ethyl-3-fluoro-benzamide

Product 1

HCID 67264158HCID 67264158, compound

Procedure

2-[5-Chloro-2-(5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-ethyl-3-fluoro-benzamide was prepared from 7-amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-ethyl-3-fluoro-benzamide in an analogous manner to Example 308c. Product isolated as a yellow foam (213 mg, 51%). LCMS (m/e) 497 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.73 (s, 1H), 8.10 (s, 1H), 7.56 (d, 1H, J=8.5 Hz), 7.40-7.35 (m, 1H), 7.34-7.25 (m, 2H), 7.21 (s, 1H), 7.10 (s, 1H), 6.96 (s, 1H), 6.72 (d, 1H, J=8.5 Hz), 6.15-6.06 (m, 1H), 3.48-3.38 (m, 2H), 2.36 (t, 2H, J=6.8 Hz), 2.08 (t, 2H, J=6.8 Hz), 1.35 (s, 6H), 1.17 (t, 3H, J=7.3 Hz).

Sources & evidence

ORD record
ord-ff5676ba0f51480cb7443e4e5b3a1123
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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