9-Ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine → HCID 66829664, compound
Reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:8]=2[O:7][CH2:6][CH2:5][CH2:4]1)[CH3:2].[CH3:15][NH:16][C:17]([C:19]1[S:20][CH:21]=[CH:22][C:23]=1[NH:24][C:25]1[C:30]([Cl:31])=[CH:29][N:28]=[C:27](Cl)[N:26]=1)=[O:18]>>[CH3:15][NH:16][C:17]([C:19]1[S:20][CH:21]=[CH:22][C:23]=1[NH:24][C:25]1[C:30]([Cl:31])=[CH:29][N:28]=[C:27]([NH:14][C:12]2[CH:11]=[CH:10][C:9]3[N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][O:7][C:8]=3[CH:13]=2)[N:26]=1)=[O:18]Participants
Procedure
3-[5-Chloro-2-(9-ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamino)-pyrimidin-4-ylamino]-thiophene-2-carboxylic acid methylamide was prepared from 9-ethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine and 3-(2,5-dichloro-pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methylamide in an analogous manner to Example 308c. Product isolated as a tan solid (124 mg, 60%). m.p.=199-201° C.; LCMS (m/e) 459 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 11.59 (s, 1H), 9.26 (s, 1H), 8.51-8.42 (m, 1H), 8.22 (d, 1H, J=4.8 Hz); 8.20 (s, 1H), 7.71 (d, 1H, J=5.3 Hz), 7.25 (s, 1H), 7.11 (d, 1H, J=9.34 Hz), 6.81 (d, 1H, J=8.8 Hz), 4.03 (t, 2H, J=5.3 Hz), 3.17 (q, 2H, J=7.0 Hz), 3.11 (t, 2H, J=5.0 Hz), 2.78 (d, 3H, J=4.3 Hz), 1.96-1.86 (m, 2H), 1.13 (t, 3H, J=7.0 Hz).
Sources & evidence
- ORD record
- ord-adafa433a8734244ab91de6433831e08
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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