3-(2-Methoxyethyl)-2,3,4,5-tetrahydro-1h-3-benzazepin-7-amine → HCID 66830100, compound

HRID 1040792Notes

Reaction equation

HRID 1040792 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1.Cl[C:18]1[N:23]=[C:22]([NH:24][CH2:25][CH:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH3:27])[C:21]([Cl:33])=[CH:20][N:19]=1>>[Cl:33][C:21]1[C:22]([NH:24][CH2:25][CH:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH3:27])=[N:23][C:18]([NH:16][C:13]2[CH:14]=[CH:15][C:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:11][CH2:10][C:9]=3[CH:12]=2)=[N:19][CH:20]=1

Participants

3

Reactant 2

HCID 574160893-(2-Methoxyethyl)-2,3,4,5-tetrahydro-1h-3-benzazepin-7-amineHCID 86633869HCID 86633869, compound

Product 1

HCID 66830100HCID 66830100, compound

Procedure

N-(2-{5-Chloro-2-[3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrimidin-4-ylamino}-1-methyl-ethyl)-methanesulfonamide was prepared from 3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine and N-[2-(2,5-dichloro-pyrimidin-4-ylamino)-1-methyl-ethyl]-methanesulfonamide in an analogous manner to Example 300. Product isolated as a white solid (96 mg, 58%). LCMS (m/e) 483 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 7.95 (s, 1H), 7.35-7.23 (m, 2H), 7.05 (d, 1H, J=8.0 Hz), 6.93 (s, 1H), 5.70-5.62 (m, 1H), 5.40-5.31 (m, 1H), 3.55 (t, 2H, J=5.7 Hz), 3.53-3.43 (m, 1H), 3.39 (s, 3H), 2.97-2.87 (m, 4H) 2.90 (s, 3H), 2.80-2.69 (m, 6H), 1.31 (d, 3H, J=6.6 Hz).

Sources & evidence

ORD record
ord-84ebce7fd279485e902f0807601c68e3
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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