HCID 136121467, compound → HCID 136121495, compound

HRID 2062319Notes

Reaction equation

HRID 2062319 reaction equation
C(OC(=O)[NH:10][CH2:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[OH:34])[N:18]=2)[CH2:13]1)C1C=CC=CC=1>[Pd].CO>[NH2:10][CH2:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[OH:34])[N:18]=2)[CH2:13]1

Participants

4

Reactant 1

HCID 136121467HCID 136121467, compound

Product 1

HCID 136121495HCID 136121495, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl((R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate (0.19 g, 0.41 mmol) and MeOH (5 mL) was stirred with Pd/C (20 mg, 10% weight of Pd on carbon) under an H2 atmosphere at ambient pressure overnight. Purification via silica gel chromatography using MeOH in CH2Cl2 (0-10%) gave 2-(4-((R)-3-(aminomethyl)pyrrolidin-1-yl)-7-methylquinazolin-2-yl)phenol (63 mg, 45%). LC/MS: m/z 335.7 (M+H)+ at 1.23 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-b578692d5f9f451596994ae37fdd0a87
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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