2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1-(4-methyl-piperazin-1-yl)-ethanone → 5-Chloro-2-(5-chloro-2-{8-methoxy-3-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide

HRID 1041129Notes

Reaction equation

HRID 1041129 reaction equation
[NH2:1][C:2]1[C:22]([O:23][CH3:24])=[CH:21][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[O:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([NH:38][C:39]2[C:44]([Cl:45])=[CH:43][N:42]=[C:41](Cl)[N:40]=2)=[C:30]([S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])[CH:31]=1>>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([NH:38][C:39]2[C:44]([Cl:45])=[CH:43][N:42]=[C:41]([NH:1][C:2]3[C:22]([O:23][CH3:24])=[CH:21][C:5]4[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]5[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]5)=[O:13])[CH2:9][CH2:10][C:4]=4[CH:3]=3)[N:40]=2)=[C:30]([S:32]([N:35]([CH3:37])[CH3:36])(=[O:33])=[O:34])[CH:31]=1

Participants

3

Reactant 2

HCID 672636672-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1-(4-methyl-piperazin-1-yl)-ethanoneHCID 866339395-Chloro-2-(2,5-dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide

Product 1

HCID 668299305-Chloro-2-(5-chloro-2-{8-methoxy-3-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide

Procedure

The title compound was prepared from 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1-(4-methyl-piperazin-1-yl)-ethanone and 5-Chloro-2-(2,5-dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide in an analogous manner to Example 61e. Product isolated as a tan foam (0.025 g, 20%). MP: 137-150° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 9.21 (s, 1H), 8.46 (d, 1H, J=8.8 Hz), 8.15 (s, 1H), 7.93 (s, 1H), 7.86 (d, 1H, J=2.5 Hz), 7.51-7.47 (m, 2H), 6.65 (s, 1H), 3.87 (s, 3H), 3.75-3.63 (m, 4H), 3.30 (s, 2H), 2.91-2.86 (m, 2H), 2.77 (s, 6H), 2.76-2.63 (m, 6H), 2.49-2.38 (m, 4H), 2.33 (s, 3H). MS: 677.18 (MH)+.

Sources & evidence

ORD record
ord-17d209d031d64fc5aec4c60319212023
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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