8-Methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamine → 5-Chloro-N(4)-(4-dimethylamino-2-methoxy-phenyl)-N(2)-[8-methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-pyrimidine-2,4-diamine

HRID 1687870Notes

Reaction equation

HRID 1687870 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][C:10]=2[O:18][CH3:19])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][O:22][C:23]1[C:24]([NH2:42])=[CH:25][C:26]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH2:29][CH2:28][C:27]=2[CH:41]=1>>[Cl:20][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][C:10]=2[O:18][CH3:19])=[N:7][C:2]([NH:42][C:24]2[C:23]([O:22][CH3:21])=[CH:41][C:27]3[CH2:28][CH2:29][N:30]([CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[CH2:31][CH2:32][C:26]=3[CH:25]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 672641368-Methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamineHCID 86634017N(1)-(2,5-Dichloro-pyrimidin-4-yl)-2-methoxy-N(4),N(4)-dimethyl-benzene-1,4-diamine

Product 1

HCID 672636955-Chloro-N(4)-(4-dimethylamino-2-methoxy-phenyl)-N(2)-[8-methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-pyrimidine-2,4-diamineYield 22%

Procedure

In an analogous manner to Example 1503, the product was prepared from N(1)-(2,5-Dichloro-pyrimidin-4-yl)-2-methoxy-N(4),N(4)-dimethyl-benzene-1,4-diamine and 8-Methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamine. Product was isolated as a light yellow foam (40 mg, 22%). mp: 115° C. (glass @ 75) MS (ESI+): 582 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.16 (s, 1H), 8.14 (s, 1H), 8.01 (s, 1H), 7.45 (s, 1H), 7.43 (s, 1H), 6.64 (s, 1H), 6.38 (s, 1H), 6.35 (s, 1H), 3.93 (s, 3H), 3.87 (s, 3H), 3.74 (t, J=5 Hz, 4H), 2.99 (s, 6H), 2.87 (m, 2H), 2.82 (m, 2H), 2.70 (t, J=7 Hz, 6H), 2.56 (m, 2H), 2.51 (m, 4H).

Sources & evidence

ORD record
ord-d90fe9a67e1d43a584690cc788fb63a9
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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