8-Amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one → HCID 86634030, compound

HRID 1041427Notes

Reaction equation

HRID 1041427 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:33]([F:34])=[CH:32][CH:31]=[CH:30][C:23]=2[C:24]([NH:26][CH2:27][C:28]#[CH:29])=[O:25])[C:18]([Cl:35])=[CH:17][N:16]=1>>[Cl:35][C:18]1[C:19]([NH:21][C:22]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:23]=2[C:24]([NH:26][CH2:27][C:28]#[CH:29])=[O:25])=[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 866339022-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-prop-2-ynyl-benzamide

Product 1

HCID 86634030HCID 86634030, compound

Procedure

2-[5-Chloro-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-8-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-prop-2-ynyl-benzamide was prepared from 8-amino-1,3,4,5-tetrahydro-benzo[b]azepin-2-one and 2-(2,5-dichloro-pyrimidin-4-ylamino)-3-fluoro-N-prop-2-ynyl-benzamide in an analogous manner to Example 308c. Product isolated as a yellow solid (36 mg, 19%). m.p.=236-241° C.; LCMS (m/e) 479 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.40 (s, 1H), 8.10 (s, 1H), 7.53 (d, 1H, J=7.4 Hz), 7.47-7.31 (m, 3H), 7.16 (s, 1H), 7.07-7.00 (m, 2H), 6.82 (d, 1H, J=8.1 Hz), 6.54-6.47 (m, 1H), 4.21-4.15 (m, 2H), 2.73 (t, 2H, J=7.3 Hz), 2.34 (t, 2H, J=7.1 Hz), 2.26-2.15 (m, 3H).

Sources & evidence

ORD record
ord-bce19d7e5f15470aa3c4fcbe93df2894
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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