2,3,4,5-Tetrahydro-benzo[b]oxepin-9-ylamine → 5-Chloro-N*4*-(2-methoxy-4-morpholin-4-yl-phenyl)-N*2*-(2,3,4,5-tetrahydrobenzo[b]oxepin-9-yl)pyrimidine-2,4-diamine

HRID 1687451Notes

Reaction equation

HRID 1687451 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[C:11]([NH2:12])[C:2]1=2.Cl[C:14]1[N:19]=[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][C:22]=2[O:33][CH3:34])[C:17]([Cl:35])=[CH:16][N:15]=1>>[Cl:35][C:17]1[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)=[CH:23][C:22]=2[O:33][CH3:34])=[N:19][C:14]([NH:12][C:11]2[C:2]3[O:1][CH2:7][CH2:6][CH2:5][CH2:4][C:3]=3[CH:8]=[CH:9][CH:10]=2)=[N:15][CH:16]=1

Participants

3

Reactant 2

HCID 137576312,3,4,5-Tetrahydro-benzo[b]oxepin-9-ylamineHCID 86633851(2,5-Dichloropyrimidin-4-yl)-(2-methoxy-4-morpholin-4-yl-phenyl)-amine

Product 1

HCID 1317295925-Chloro-N*4*-(2-methoxy-4-morpholin-4-yl-phenyl)-N*2*-(2,3,4,5-tetrahydrobenzo[b]oxepin-9-yl)pyrimidine-2,4-diamine

Procedure

The title compound was prepared from 2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine and (2,5-dichloro-pyrimidin-4-yl)-(2-methoxy-4-morpholin-4-yl-phenyl)-amine in an analogous manner to Example 179. Product was isolated as a light brown solid (51 mg, 40%). LCMS (m/e) 482 (M+H); 1H NMR (400 MHz, DMSO-d6) δ 8.88 (broad s, 1H), 8.43 (broad s, 1H), 8.28 (s, 1H), 7.66 (d, 1H, J=8 Hz), 7.37 (d, 1H, J=9 Hz), 6.80 (d, 1H, J=7.58 Hz), 6.71 (s, 1H), 6.67 (dd, 1H, J=7.58, 8 Hz), 6.54 (d, 1H, J=8 Hz), 3.94 (m, 2H), 3.78 (m, 6H), 3.18 (m, 5H), 2.70 (m, 2H), 1.89 (m, 2H), 1.62 (m, 2H).

Sources & evidence

ORD record
ord-0358adf8b26045ec938d45b7b7daec05
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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