1-((4-methoxyphenyl)methyl)-1H-pyrazol-4-amine → 2-[5-[1-(4-Methoxy-benzyl)-1H-pyrazol-4-ylcarbamoyl]-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]-indole-1-carboxylic acid tert-butyl ester

HRID 1406394Notes

Reaction equation

HRID 1406394 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[C:18](=[O:34])[N:19]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:20]=[C:21]([C:23]([OH:25])=O)[CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:35][O:36][C:37]1[CH:49]=[CH:48][C:40]([CH2:41][N:42]2[CH:46]=[C:45]([NH2:47])[CH:44]=[N:43]2)=[CH:39][CH:38]=1>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[C:18](=[O:34])[N:19]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:33])[CH3:31])[CH:20]=[C:21]([C:23](=[O:25])[NH:47][C:45]2[CH:44]=[N:43][N:42]([CH2:41][C:40]3[CH:48]=[CH:49][C:37]([O:36][CH3:35])=[CH:38][CH:39]=3)[CH:46]=2)[CH:22]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 283739871-((4-methoxyphenyl)methyl)-1H-pyrazol-4-amineHCID 581173092-[5-Carboxy-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 668530952-[5-[1-(4-Methoxy-benzyl)-1H-pyrazol-4-ylcarbamoyl]-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]-indole-1-carboxylic acid tert-butyl ester

Procedure

The title compound was prepared according to the experimental used in Example 1, Step 4 using intermediate (1c) and 1-(4-methoxy-benzyl)-1H-pyrazol-4-ylamine. After the usual aqueous work up, the resultant crude product was purified by flash chromatography on SiO2 eluting with hexane—50% ethyl acetate/hexane. This afforded the title compound as a pink solid, 180 mg, 50%.

Workup

  1. customThe title compound was prepared
  2. customAfter the usual aqueous work up, the resultant crude product was purified by flash chromatography on SiO2 eluting with hexane—50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b52b00bce84a48cc8a84483bb3b9cc2e
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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