7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one → 3-[5-Chloro-2-(5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-4-methyl-thiophene-2-carboxylic acid methyl amide

HRID 1041554Notes

Reaction equation

HRID 1041554 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.[CH3:16][NH:17][C:18]([C:20]1[S:21][CH:22]=[C:23]([CH3:34])[C:24]=1[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[C:28](Cl)[N:27]=1)=[O:19]>>[CH3:16][NH:17][C:18]([C:20]1[S:21][CH:22]=[C:23]([CH3:34])[C:24]=1[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[C:28]([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:27]=1)=[O:19]

Participants

3

Reactant 2

HCID 578538307-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneHCID 866340193-(2,5-dichloropyrimidin-4-ylamino)-N,4-dimethylthiophene-2-carboxamide

Product 1

HCID 668302503-[5-Chloro-2-(5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamino)-pyrimidin-4-ylamino]-4-methyl-thiophene-2-carboxylic acid methyl amide

Procedure

The title compound was prepared in an analogous manner to the preparation of example 381 by combining 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one and 3-(2,5-Dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide to yield an orange solid (11%). LCMS: m/z=485.08 (M+H+), 1H NMR (400 MHz, CDCl3) δ 8.91 (s, 1H), 8.05 (m, 2H), 7.65 (s, 1H), 7.45 (d, 1H, J=8.6 Hz), 7.29 (m, 1H), 7.01 (s, 1H), 6.75 (d, 1H, J=8.6 Hz), 6.11 (m, 1H), 3.52 (m, 3H), 2.93 (d, 3H, J=4.8 Hz), 2.35 (m, 2H), 2.06 (m, 2H), 1.31 (s, 6H).

Sources & evidence

ORD record
ord-d65883f07ea34f85be6bc44f9ce59d90
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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