tert-Butyl 4-(4-aminophenylsulfonyl)piperazine-1-carboxylate → tert-butyl 4-(4-(4-(5-(3-(trifluoromethyl)phenylcarbamoyl)naphthalen-1-yloxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-6-ylamino)phenylsulfonyl)piperazine-1-carboxylate
Reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:5]2=[C:4]([O:19][C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)=[O:31])[CH:3]=1.[NH2:43][C:44]1[CH:49]=[CH:48][C:47]([S:50]([N:53]2[CH2:58][CH2:57][N:56]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:55][CH2:54]2)(=[O:52])=[O:51])=[CH:46][CH:45]=1>>[F:40][C:39]([F:42])([F:41])[C:35]1[CH:34]=[C:33]([NH:32][C:30]([C:25]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:26]=2[CH:27]=[CH:28][CH:29]=[C:20]3[O:19][C:4]2[CH:3]=[C:2]([NH:43][C:44]3[CH:49]=[CH:48][C:47]([S:50]([N:53]4[CH2:58][CH2:57][N:56]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:55][CH2:54]4)(=[O:51])=[O:52])=[CH:46][CH:45]=3)[N:7]=[C:6]3[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:18])[CH3:16])[CH:9]=[CH:10][C:5]=23)=[O:31])[CH:38]=[CH:37][CH:36]=1Participants
3
Reactant 2
Product 1
Procedure
tert-butyl 4-(4-(4-(5-(3-(trifluoromethyl)phenylcarbamoyl)naphthalen-1-yloxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-6-ylamino)phenylsulfonyl)piperazine-1-carboxylate (42 mg, 70% yield) was prepared as described for Example 5-B starting from 5-(6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1-naphthamide (40 mg, 0.065 mmol) and tert-butyl 4-(4-aminophenylsulfonyl)piperazine-1-carboxylate (22 mg, 0.065 mmol). MS m/z: 917 [M+1].
Sources & evidence
- ORD record
- ord-e2c82ab167994dbea70ea17273b4a6a2
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09358231B2
Reaction notes
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