5,5-Dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine → HCID 25157032, compound

HRID 1687465Notes

Reaction equation

HRID 1687465 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.[C:15]([CH2:17][CH2:18][NH:19][C:20](=[O:36])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:28]1[C:33]([Cl:34])=[CH:32][N:31]=[C:30](Cl)[N:29]=1)#[N:16]>>[Cl:34][C:33]1[C:28]([NH:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([NH:19][CH2:18][CH2:17][C:15]#[N:16])=[O:36])=[N:29][C:30]([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:31][CH:32]=1

Participants

3

Reactant 2

HCID 672643345,5-Dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamineHCID 86633943HCID 86633943, compound

Product 1

HCID 25157032HCID 25157032, compound

Procedure

The title compound was prepared from 5,5-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-9-ylamine and N-(2-cyano-ethyl)-2-(2,5-dichloro-pyrimidin-4-ylamino)-benzamide in an analogous manner to Example 179. Product was isolated as a golden brown solid (50 mg, 50%). LCMS (m/e) 491 (M+H); 1H NMR (400 MHz, CDCl3) δ 10.78 (s, 1H), 8.69 (d, 1H, J=8.6 Hz), 8.25 (d, 1H, J=7.8 Hz), 8.12 (s, 1H), 7.80 (s, 1H), 7.53 (m, 2H), 7.12 (t, 1H, J=7.8 Hz), 6.95 (m, 2H), 6.74 (m, 1H), 4.01 (t, 2H, J=5 Hz), 3.73 (dd, 2H, J=6, 12 Hz), 2.76 (t, 2H, J=6 Hz), 2.08 (m, 2H), 1.69 (t, 2H, J=6 Hz), 1.40 (s, 6H).

Sources & evidence

ORD record
ord-cdeb317687894dc881a1f6e56f2d0236
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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