5,5-Dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine → 2-[5-Chloro-2-(5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamino)-pyrimidin-4-ylamino]-N-ethyl-3-fluoro-benzamide

HRID 1041157Notes

Reaction equation

HRID 1041157 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][CH2:6][O:5][C:4]2[C:9]([NH2:13])=[CH:10][CH:11]=[CH:12][C:3]1=2.Cl[C:16]1[N:21]=[C:20]([NH:22][C:23]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:24]=2[C:25]([NH:27][CH2:28][CH3:29])=[O:26])[C:19]([Cl:35])=[CH:18][N:17]=1>>[Cl:35][C:19]1[C:20]([NH:22][C:23]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:24]=2[C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[N:21][C:16]([NH:13][C:9]2[C:4]3[O:5][CH2:6][CH2:7][CH2:8][C:2]([CH3:14])([CH3:1])[C:3]=3[CH:12]=[CH:11][CH:10]=2)=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 672643345,5-Dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamineHCID 866339272-(2,5-Dichloro-pyrimidin-4-ylamino)-N-ethyl-3-fluoro-benzamide

Product 1

HCID 251570302-[5-Chloro-2-(5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamino)-pyrimidin-4-ylamino]-N-ethyl-3-fluoro-benzamide

Procedure

The title compound was prepared from 5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-ethyl-3-fluoro-benzamide in an analogous manner to Example 179. Product isolated as a tan solid (30 mg, 30%). LCMS (m/e) 484 (M+H); 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 8.08 (s, 1H), 7.92 (d, 1H, J=8 Hz), 7.78 (s, 1H), 7.33 (m, 3H), 6.84 (d, 1H, J=7.8 Hz), 6.74 (t, 1H, J=8, 7.8 Hz), 6.05 (m, 1H), 3.96 (m, 2H), 3.38 (m, 2H), 2.04 (m, 2H), 1.66 (m, 2H) 1.34 (s, 6H), 1.11 (t, 3H, J=7.3 Hz).

Sources & evidence

ORD record
ord-239bcaa43e0d4282a15a50926ce96ecf
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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