HCID 66707370, compound → HCID 66707309, compound
Reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][C:8]1[CH:9]=[N:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:12]=1C)([CH3:4])([CH3:3])[CH3:2].[C:25]([O:29][C:30](=[O:49])[CH2:31][C:32]1[CH:33]=[N:34][N:35]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-])=O)=[CH:42][CH:41]=2)[C:36]=1[CH2:37]C)([CH3:28])([CH3:27])[CH3:26].COC(=O)CC1C(C)=NN(C([N+]([O-])=O)C2C=CC=CC=2)C=1C>>[C:1]([O:5][C:6](=[O:24])[CH2:7][C:8]1[C:9]([CH3:25])=[N:10][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH:12]=1)([CH3:2])([CH3:3])[CH3:4].[C:25]([O:29][C:30](=[O:49])[CH2:31][C:32]1[CH:33]=[N:34][N:35]([CH2:39][C:40]2[CH:41]=[CH:42][C:43]([NH2:46])=[CH:44][CH:45]=2)[C:36]=1[CH3:37])([CH3:28])([CH3:26])[CH3:27]Participants
Procedure
The following examples can be prepared in analogous fashion to example 1.1, employing in the reduction step [5-methyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid tert-butyl ester or in the case of example 2.59 [5-ethyl-1-(4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid tert-butyl ester (preparation according to WO2008/138876) instead of [3,5-dimethyl-1-(nitrobenzyl)-1H-pyrazol-4-yl-acetic acid methyl ester and employing in the amide coupling the corresponding carboxylic acids as coupling partners. Each example except for example 2.59 is a single regioisomer; the required intermediates [1-(4-amino-benzyl)-3-methyl-1H-pyrazol-4-yl]-acetic acid tert-butyl ester and [1-(4-amino-benzyl)-5-methyl-1H-pyrazol-4-yl]-acetic acid tert-butyl ester are obtained in a single reaction and are separable by MPLC.
Sources & evidence
- ORD record
- ord-171fe046bda74d6ca47f20f17d3f678e
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791272B2
Reaction notes
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