(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → (S)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-(1-trityl-1H-imidazol-4-yl)-1,2,4-oxadiazole-5-carboxamide

HRID 872917Notes

Reaction equation

HRID 872917 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[N:29]=[C:28]([C:30]([OH:32])=O)[O:27][N:26]=2)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:33][C@@H:34]([CH3:50])[CH2:35][N:36]1[CH:40]=[CH:39][C:38]([C:41]2[CH:48]=[CH:47][C:44]([C:45]#[N:46])=[C:43]([Cl:49])[CH:42]=2)=[N:37]1>>[Cl:49][C:43]1[CH:42]=[C:41]([C:38]2[CH:39]=[CH:40][N:36]([CH2:35][C@@H:34]([NH:33][C:30]([C:28]3[O:27][N:26]=[C:25]([C:23]4[N:22]=[CH:21][N:20]([C:1]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[CH:24]=4)[N:29]=3)=[O:32])[CH3:50])[N:37]=2)[CH:48]=[CH:47][C:44]=1[C:45]#[N:46]

Participants

3

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 671735983-(1-trityl-1H-imidazol-4-yl)-1,2,4-oxadiazole-5-carboxylic acid

Product 1

HCID 70656354(S)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-(1-trityl-1H-imidazol-4-yl)-1,2,4-oxadiazole-5-carboxamide

Procedure

The title compound was prepared using the method of Example 34(d) starting from 3-(1-trityl-1H-imidazol-4-yl)-1,2,4-oxadiazole-5-carboxylic acid (0.211 g, 0.499 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.1 g, 0.384 mmol). The product was purified by flash chromatography. LC-MS: [M+1]=666.142.

Workup

  1. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-0379976d63994ab3b35a5eaec34064d0
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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