3-(2,2-Difluoro-propyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine → HCID 67264363, compound

HRID 1041090Notes

Reaction equation

HRID 1041090 reaction equation
[F:1][C:2]([F:19])([CH3:18])[CH2:3][N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([NH2:17])[C:13]([O:15][CH3:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1.Cl[C:21]1[N:26]=[C:25]([NH:27][C@@H:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]2[NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[C:24]([Cl:39])=[CH:23][N:22]=1>>[Cl:39][C:24]1[C:25]([NH:27][C@@H:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]2[NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[N:26][C:21]([NH:17][C:12]2[C:13]([O:15][CH3:16])=[CH:14][C:7]3[CH2:6][CH2:5][N:4]([CH2:3][C:2]([F:1])([F:19])[CH3:18])[CH2:10][CH2:9][C:8]=3[CH:11]=2)=[N:22][CH:23]=1

Participants

3

Reactant 2

HCID 672635183-(2,2-Difluoro-propyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamineHCID 86633854N-[(1R,2R)-2-(2,5-dichloropyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide

Product 1

HCID 67264363HCID 67264363, compound

Procedure

The title compound was prepared from 3-(2,2-Difluoro-propyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine and N-[(1R,2R)-2-(2,5-Dichloro-pyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide in a manner analogous to Example 61e. Product isolated as an off-white solid (0.011 g, 13%). MP: 94-115° C. 1HNMR (400 MHz, CDCl3, δ, ppm): 7.97 (s, 1H), 7.94 (s, 1H), 7.33 (br s, 1H), 6.64 (s, 1H), 5.36 (d, 1H, J=7.6 Hz), 5.29 (d, 1H, J=7.1 Hz), 3.99-3.89 (m, 1H), 3.87 (s, 3H), 3.29-3.18 (m, 1H), 2.91-2.80 (m, 10H), 2.79 (s, 3H), 2.27-2.15 (m, 2H), 1.86-1.77 (m, 2H), 1.68 (t, 3H, J=18.8 Hz), 1.40-1.32 (m, 4H). MS: 573 (MH)+.

Sources & evidence

ORD record
ord-2ddaf49b8454479b98bd92990d61b2b0
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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