5,5-Dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine → {2-[5-Chloro-2-(5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamino)-pyrimidin-4-ylamino]-phenoxy}-acetonitrile

HRID 1041163Notes

Reaction equation

HRID 1041163 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:32]=[CH:31][CH:30]=[CH:29][C:24]=2[O:25][CH2:26][C:27]#[N:28])[C:19]([Cl:33])=[CH:18][N:17]=1>>[Cl:33][C:19]1[C:20]([NH:22][C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=2[O:25][CH2:26][C:27]#[N:28])=[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 86633910[2-(2,5-Dichloropyrimidin-4-ylamino)-phenoxy]acetonitrile

Product 1

HCID 25159009{2-[5-Chloro-2-(5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamino)-pyrimidin-4-ylamino]-phenoxy}-acetonitrile

Procedure

The title compound was prepared from 5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine and [2-(2,5-dichloro-pyrimidin-4-ylamino)-phenoxy]-acetonitrile in an analogous manner to Example 179 heating at 130° C. Product was isolated as a white solid (26 mg, 34%). LCMS (m/e) 450 (M+H); 1H NMR (400 MHz, CDCl3) δ 10.58 (broad s, 1H), 8.15 (s, 1H), 8.08 (d, 1H, J=8.1 Hz), 7.93 (s, 1H), 7.55 (d, 1H, J=7.6 Hz), 7.19 (m, 2H), 7.03 (d, 1H, J=8.34 Hz), 6.97 (m, 2H), 4.88 (s, 2H), 4.02 (m, 2H), 2.01 (m, 2H), 1.67 (m, 2H), 1.37 (s, 6H).

Sources & evidence

ORD record
ord-85f3c8960b8441ec9025d2dbc8f11a8c
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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