2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)ethan-1-ol → 1-(2-{5-Chloro-2-[3-(2-hydroxy-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamino]-pyrimidin-4-ylamino}-benzenesulfonyl)-pyrrolidin-3-ol

HRID 1041542Notes

Reaction equation

HRID 1041542 reaction equation
[NH2:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][OH:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C([Si](C)(C)[O:23][CH:24]1[CH2:28][CH2:27][N:26]([S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[NH:38][C:39]2[C:44]([Cl:45])=[CH:43][N:42]=[C:41](Cl)[N:40]=2)(=[O:31])=[O:30])[CH2:25]1)(C)(C)C>>[Cl:45][C:44]1[C:39]([NH:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[S:29]([N:26]2[CH2:27][CH2:28][CH:24]([OH:23])[CH2:25]2)(=[O:30])=[O:31])=[N:40][C:41]([NH:1][C:2]2[C:15]([O:16][CH3:17])=[CH:14][C:5]3[CH2:6][CH2:7][N:8]([CH2:11][CH2:12][OH:13])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:42][CH:43]=1

Participants

3

Reactant 2

HCID 574161162-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)ethan-1-olHCID 86634052HCID 86634052, compound

Product 1

HCID 668306831-(2-{5-Chloro-2-[3-(2-hydroxy-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamino]-pyrimidin-4-ylamino}-benzenesulfonyl)-pyrrolidin-3-olYield 22%

Procedure

In an analogous manner to Example 1534, the product was prepared from 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-ethanol and {2-[3-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-1-sulfonyl]-phenyl}-(2,5-dichloro-pyrimidin-4-yl)-amine. Product was isolated as a white foam (25 mg, 22%). MS (ESI+): 589 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 9.33 (s, 1H), 8.48 (d, J=8 Hz, 1H), 8.17 (s, 1H), 8.01 (s, 1H), 7.97 (d, J=8 Hz, 1H), 7.55 (m, 2H), 7.25 (m, 1H), 6.66 (s, 1H), 4.37 (br s, 1H), 3.89 (s, 4H), 3.65 (t, J=9 Hz, 2H), 3.42 (m, 3H), 3.41 (d, 1H), 2.87 (m, 2H), 2.72-2.66 (m, 8H), 1.97 (m, 1H), 1.86 (m, 1H).

Sources & evidence

ORD record
ord-bb719fef679545df95e9a9ab38d80eb7
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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