HCID 67286074, compound → HCID 49842162, compound

HRID 869336Notes

Reaction equation

HRID 869336 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH3:32])[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](/[CH:23]=[CH:24]/[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=4)[N:18]=3)=[CH:16][C:10]=2[C:9]1=[O:33])=O)(C)(C)C>Cl.O1CCOCC1>[Cl:31][C:27]1[CH:26]=[C:25](/[CH:24]=[CH:23]/[C:19]2[N:18]=[C:17]([C:15]3[N:14]([CH3:32])[C:11]4[CH2:12][CH2:13][NH:8][C:9](=[O:33])[C:10]=4[CH:16]=3)[CH:22]=[CH:21][N:20]=2)[CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 67286074HCID 67286074, compound

Product 1

HCID 49842162HCID 49842162, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A suspension of 2-{2-[(E)-2-(3-Chloro-phenyl)-vinyl]-pyrimidin-4-yl}-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.050 g, 0.107 mmol) in 4M HCl/dioxane (2.0 ml) was stirred at room temperature for 1 h. The solvent was removed under vacuum and the product was purified by crystallisation from methanol, yielding 2-{2-[(E)-2-(3-Chloro-phenyl)-vinyl]-pyrimidin-4-yl}-1-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one as a yellow solid (0.015 g, 0.041 mmol, 38%).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe product was purified by crystallisation from methanol

Sources & evidence

ORD record
ord-ec8820f1e03c471c9e9951995e406ea0
Source dataset
uspto-grants-2015_03
Patent number
US08969366B2

Reaction notes

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