5-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester → 5-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 1025571Notes

Reaction equation

HRID 1025571 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:36])[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]3[N:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:22]=4)[C:17]3=[O:30])[C:11]=2[CH2:31][O:32]C(=O)C)=[CH:8][CH:9]=1)=[O:4]>N.CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:36])[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N:16]3[N:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:22]=4)[C:17]3=[O:30])[C:11]=2[CH2:31][OH:32])=[CH:8][CH:9]=1)=[O:4]

Participants

3

Reactant 1

HCID 710081245-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester

Product 1

HCID 710085895-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl esterYield 69.3%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

A mixture of 5-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (237 mg, 0.486 mmol) in saturated NH3/MeOH (20 mL) was stirred at room temperature for 48 h. The mixture was evaporated to dryness to give 5-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (150 mg, yield 68%) as a yellow solid. LC-MS calcd for C26H27N3O4 (m/e) 445.20, obsd 913 [2M+Na]+.

Workup

  1. customThe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-0bb211599c494378aef0018085d7cabb
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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