3-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine → N-{2-[5-Chloro-2-(3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-propyl}-methanesulfonamide

HRID 1687103Notes

Reaction equation

HRID 1687103 reaction equation
[CH2:1]([N:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:6]=2[CH2:5][CH2:4]1)[CH3:2].Cl[C:16]1[N:21]=[C:20]([NH:22][CH:23]([CH3:30])[CH2:24][NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:19]([Cl:31])=[CH:18][N:17]=1>>[Cl:31][C:19]1[C:20]([NH:22][CH:23]([CH3:30])[CH2:24][NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[N:21][C:16]([NH:14][C:11]2[CH:12]=[CH:13][C:6]3[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:9][CH2:8][C:7]=3[CH:10]=2)=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 189434013-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamineHCID 86633870N-[2-(2,5-dichloro-pyrimidin-4-ylamino)-propyl]-methanesulfonamide

Product 1

HCID 66829837N-{2-[5-Chloro-2-(3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-propyl}-methanesulfonamide

Procedure

N-{2-[5-Chloro-2-(3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-propyl}-methanesulfonamide was prepared from 3-ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine and N-[2-(2,5-dichloro-pyrimidin-4-ylamino)-propyl]-methanesulfonamide in an analogous manner to Example 300b. Product isolated as a pale pink foam (84 mg, 41%). LCMS (m/e) 453 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 7.94 (s, 1H), 7.32 (d, 1H, J=7.7 Hz), 7.25 (s, 1H), 7.06 (d, 1H, J=8.0 Hz), 6.90 (s, 1H), 5.30-5.17 (m, 2H), 4.41-4.31 (m, 1H), 3.46-3.37 (m, 1H), 3.30-3.19 (m, 1H), 3.33-2.86 (m, 4H), 2.91 (s, 3H), 2.72-2.60 (m, 5H), 2.59 (q, 2H, J=6.9 Hz), 1.37 (d, 3H, J=5.9 Hz), 1.12 (t, 3H, J=6.9 Hz).

Sources & evidence

ORD record
ord-55168757ca6444488661e549bd5a3bfa
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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