5,5-Dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine → 5-Chloro-N*2*-(5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-yl)-N*4*-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-pyrimidine-2,4-diamine

HRID 1687467Notes

Reaction equation

HRID 1687467 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][CH2:6][O:5][C:4]2[C:9]([NH2:13])=[CH:10][CH:11]=[CH:12][C:3]1=2.Cl[C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=2)[C:19]([Cl:35])=[CH:18][N:17]=1>>[Cl:35][C:19]1[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=2)=[N:21][C:16]([NH:13][C:9]2[C:4]3[O:5][CH2:6][CH2:7][CH2:8][C:2]([CH3:14])([CH3:1])[C:3]=3[CH:12]=[CH:11][CH:10]=2)=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 672643345,5-Dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamineHCID 86633891(2,5-Dichloro-pyrimidin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-amine

Product 1

HCID 1317295985-Chloro-N*2*-(5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-yl)-N*4*-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-pyrimidine-2,4-diamine

Procedure

The title compound was prepared from 5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine and (2,5-dichloro-pyrimidin-4-yl)-[2-(1-methyl-1H-imidazol-2-yl)-phenyl]-amine in an analogous manner to Example 179 heating at 130° C. Product was isolated as a pink foam (42 mg, 57%). LCMS (m/e) 475 (M+H); 1H NMR (400 MHz, CDCl3) δ 10.66 (s, 1H), 8.60 (d, 1H, J=8.3 Hz), 8.32 (d, 1H, J=7.8 Hz), 8.05 (s, 1H), 7.78 (s, 1H), 7.43 (m, 2H), 7.21 (m, 2H), 6.95 (m, 3H), 4.01 (m, 2H), 3.76 (s, 3H), 2.07 (m, 2H), 1.69 (m, 2H), 1.39 (s, 6H).

Sources & evidence

ORD record
ord-48c3e7e34f354368b0a006b9672d8932
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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