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

HRID 1687892Notes

Reaction equation

HRID 1687892 reaction equation
[NH2:1][C:2]1[C:17]([O:18][CH3:19])=[CH:16][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C([Si](C)(C)[O:25][C@@H:26]1[CH2:30][CH2:29][N:28]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[NH:40][C:41]2[C:46]([Cl:47])=[CH:45][N:44]=[C:43](Cl)[N:42]=2)(=[O:33])=[O:32])[CH2:27]1)(C)(C)C>>[Cl:47][C:46]1[C:41]([NH:40][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[S:31]([N:28]2[CH2:29][CH2:30][C@@H:26]([OH:25])[CH2:27]2)(=[O:32])=[O:33])=[N:42][C:43]([NH:1][C:2]2[C:17]([O:18][CH3:19])=[CH:16][C:5]3[CH2:6][CH2:7][N:8]([CH2:11][C:12]([OH:14])([CH3:15])[CH3:13])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:44][CH:45]=1

Participants

3

Reactant 2

HCID 672639621-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-2-methyl-propan-2-olHCID 86633953{2-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-1-sulfonyl]-phenyl}-(2,5-dichloro-pyrimidin-4-yl)-amine

Product 1

HCID 66830432(R)-1-(2-{5-Chloro-2-[3-(2-hydroxy-2-methyl-propyl)-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ylamino]-pyrimidin-4-ylamino}-benzenesulfonyl)-pyrrolidin-3-olYield 47%

Procedure

In an analogous manner to Example 1534, the product was prepared from 1-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-2-methyl-propan-2-ol and {2-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-1-sulfonyl]-phenyl}-(2,5-dichloro-pyrimidin-4-yl)-amine. Product was isolated as white solid (58 mg, 47%). mp: 205-206° C., MS (ESI+): 617 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 9.33 (s, 1H), 8.48 (d, J=8 Hz, 1H), 8.17 (s, 1H), 7.97 (m, 2H), 7.53 (m, 2H), 7.25 (m, 1H), 6.65 (s, 1H), 3.60 (br s, 1H), 3.89 (s, 3H), 3.42 (q, 6 Hz, 3H), 3.30 (m, 2H), 2.87-2.72 (m, 8H), 2.48 (s, 2H), 1.95 (m, 1H), 1.88 (m, 1H), 1.57 (s, 6H), 1.22 (s, 6H).

Sources & evidence

ORD record
ord-e6f0de3d2c0b4aadb7c9fe57e6290adf
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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