3-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester → 3-[5-Chloro-4-(2-methylcarbamoyl-thiophen-3-ylamino)-pyrimidin-2-ylamino]-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:18][NH:19][C:20]([C:22]1[S:23][CH:24]=[CH:25][C:26]=1[NH:27][C:28]1[C:33]([Cl:34])=[CH:32][N:31]=[C:30](Cl)[N:29]=1)=[O:21]>>[CH2:1]([O:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][C:30]3[N:29]=[C:28]([NH:27][C:26]4[CH:25]=[CH:24][S:23][C:22]=4[C:20](=[O:21])[NH:19][CH3:18])[C:33]([Cl:34])=[CH:32][N:31]=3)=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 3-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester and 3-(2,5-dichloro-pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methylamide in an analogous manner to Example 1410. Product isolated as an orange foam (155 mg, 77%). LCMS (m/e) 503 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 11.32 (bs, 1H), 8.38 (bs, 1H), 8.13 (s, 1H), 7.45-7.27 (m, 2H), 7.21-7.05 (m, 2H), 7.01 (s, 1H), 5.81-5.69 (m, 1H), 4.33-4.05 (m, 4H), 3.90-3.65 (m, 2H), 3.03 (d, 3H, J=4.7 Hz), 2.17-2.02 (m, 2H), 1.42-1.14 (m, 3H).
Sources & evidence
- ORD record
- ord-adb2a123c0a140ab90e5cbfef1bb0124
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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