8-Amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one → 8-[5-Chloro-4-(2-fluoro-6-methanesulfonyl-phenylamino)-pyrimidin-2-ylamino]-1,3,4,5-tetrahydro-1-benzazepin-2-one

HRID 1687618Notes

Reaction equation

HRID 1687618 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.Cl[C:15]1[N:20]=[C:19]([NH:21][C:22]2[C:27]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:25]=[CH:24][C:23]=2[F:32])[C:18]([Cl:33])=[CH:17][N:16]=1>>[Cl:33][C:18]1[C:19]([NH:21][C:22]2[C:27]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:25]=[CH:24][C:23]=2[F:32])=[N:20][C:15]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[NH:7][C:6]=3[CH:13]=2)=[N:16][CH:17]=1

Participants

3

Reactant 2

HCID 46151688-Amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 86633988(2,5-Dichloro-pyrimidin-4-yl)-(2-fluoro-6-methanesulfonyl-phenyl)-amine

Product 1

HCID 672642088-[5-Chloro-4-(2-fluoro-6-methanesulfonyl-phenylamino)-pyrimidin-2-ylamino]-1,3,4,5-tetrahydro-1-benzazepin-2-one

Procedure

Title compound was prepared from 8-Amino-1,3,4,5-tetrahydro-benzo[b]azepin-2-one and (2,5-Dichloro-pyrimidin-4-yl)-(2-fluoro-6-methanesulfonyl-phenyl)-amine in an analogous manner to Example 1221d. Product isolated as an off-white solid (52 mg, 41%). MP=242-245, LCMS 478.05 (M+H), HPLC purity 93%, 1H-NMR (DMSO-d6, 400 MHz) δ 9.50 (s, 1H), 9.19 (s, 1H), 8.89 (s, 1H), 8.20 (s, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.75-7.72 (m, 1H), 7.67-7.64 (m, 1H), 7.02 (d, J=8.0 Hz, 1H), 6.93 (s, 1H), 6.84 (d, J=8.0 Hz, 1H), 3.21 (s, 3H), 2.55-2.51 (m, 2H), 2.07-2.04 (m, 4H).

Sources & evidence

ORD record
ord-4b37162cd2de498c94c3ec955081f4e3
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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