2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)ethan-1-ol → 2-(7-{5-Chloro-4-[2-(pyrrolidine-1-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-ethanol

HRID 1041535Notes

Reaction equation

HRID 1041535 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])[C:5]([Cl:23])=[CH:4][N:3]=1.[NH2:24][C:25]1[C:38]([O:39][CH3:40])=[CH:37][C:28]2[CH2:29][CH2:30][N:31]([CH2:34][CH2:35][OH:36])[CH2:32][CH2:33][C:27]=2[CH:26]=1>>[Cl:23][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])=[N:7][C:2]([NH:24][C:25]2[C:38]([O:39][CH3:40])=[CH:37][C:28]3[CH2:29][CH2:30][N:31]([CH2:34][CH2:35][OH:36])[CH2:32][CH2:33][C:27]=3[CH:26]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 574161162-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)ethan-1-olHCID 86633907HCID 86633907, compound

Product 1

HCID 668305412-(7-{5-Chloro-4-[2-(pyrrolidine-1-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-ethanolYield 43%

Procedure

In an analogous manner to Example 1534, the product was prepared from (2,5-Dichloro-pyrimidin-4-yl)-[2-(pyrrolidine-1-sulfonyl)-phenyl]-amine and 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-ethanol. The product was isolated as a light yellow foam (40 mg, 43%). mp: 110° C., MS (ESI+): 573 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 9.44 (s, 1H), 8.55 (d, J=8 Hz, 1H), 8.16 (s, 1H), 8.04 (s, 1H), 7.96 (d, J=8 Hz, 1H), 7.56 (t, J=8 Hz, 1H), 7.52 (s, 1H), 7.26 (m, 1H), 6.67 (s, 1H), 3.89 (s, 3H), 3.66 (t, 2H), 3.28 (t, J=5 Hz, 4H), 2.89 (t, 2H), 2.74-2.69 (m, 8H), 1.80 (m, 4H).

Sources & evidence

ORD record
ord-6de382a9f8d046d2aede52f42b5a618a
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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