2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide → 2-{5-Chloro-2-[8-methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamide

HRID 1041517Notes

Reaction equation

HRID 1041517 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([Cl:19])=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[C:23]([NH2:41])=[CH:24][C:25]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH2:28][CH2:27][C:26]=2[CH:40]=1>>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])=[N:7][C:2]([NH:41][C:23]2[C:22]([O:21][CH3:20])=[CH:40][C:26]3[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)[CH2:30][CH2:31][C:25]=3[CH:24]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 672641368-Methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamine

Product 1

HCID 668304872-{5-Chloro-2-[8-methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamideYield 9%

Procedure

In an analogous manner to Example 1503, the product was prepared from 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide and 8-Methoxy-3-(2-morpholin-4-yl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamine. Product isolated as and off-white foam (10 mg, 9%). MS (ESI+): 566 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 11.02 (s, 1H), 8.69 (d, J=8 Hz, 1H), 8.12 (s, 1H), 8.10 (s, 1H), 7.52-7.43 (m, 3H), 7.09 (t, 8 Hz, 1H), 6.66 (s, 1H), 6.25 (d, J=4 Hz, 1H), 3.88 (s, 3H), 3.74 (t, J=4.5, 4H), 3.05 (d, J=5 Hz, 3H), 2.88 (br s, 2H), 2.79 (br s, 2H), 2.71 (br s, 6H), 2.56 (m, 2H), 2.52 (m, 4H).

Sources & evidence

ORD record
ord-e819ef9aece64515ba09bc16b89b04da
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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