1,1'-Carbonyldiimidazole → Urea 4-{2-[4-(3-tert-butyl-5-{3-[4-(pyridin-3-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-phenoxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[C:27]([NH2:28])=[CH:26][C:25]([C:29]([CH3:32])([CH3:31])[CH3:30])=[N:24]3)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)[CH:34]=1.C1N=C[N:49]([C:52]([N:54]2C=NC=C2)=[O:53])C=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([N:23]3[C:27]([NH:28][C:52]([NH:46][C:43]4[CH:44]=[CH:45][C:40]([O:39][C:35]5[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=5)=[CH:41][CH:42]=4)=[O:53])=[CH:26][C:25]([C:29]([CH3:32])([CH3:31])[CH3:30])=[N:24]3)=[CH:21][CH:22]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2].[NH2:49][C:52]([NH2:54])=[O:53]Participants
4
Reactant 3
Product 1
Procedure
4-{2-[4-(5-Amino-3-tert-butyl-pyrazol-1-yl)-phenoxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester was coupled with 4-(pyridin-3-yloxy)phenylamine by reaction with CDI in a similar manner to that described above, to provide the urea 4-{2-[4-(3-tert-butyl-5-{3-[4-(pyridin-3-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-phenoxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (LC-MS [M+H]+=655, RT=3.51 min).
Sources & evidence
- ORD record
- ord-0e76875f208b478b8e4526e704c820c4
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207166B2
Reaction notes
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