Sodium Hydroxide → 4-(tert-Butoxycarbonyl(2,4-dimethoxybenzyl)amino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxylic acid

HRID 220345Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[O:38][CH3:39])[C:9]1[N:14]=[C:13]2[N:15]([CH2:23][CH3:24])[C:16]([C:18]([O:20]CC)=[O:19])=[CH:17][C:12]2=[C:11]2[N:25]([CH3:28])[CH:26]=[N:27][C:10]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[O:38][CH3:39])[C:9]1[N:14]=[C:13]2[N:15]([CH2:23][CH3:24])[C:16]([C:18]([OH:20])=[O:19])=[CH:17][C:12]2=[C:11]2[N:25]([CH3:28])[CH:26]=[N:27][C:10]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 4-(tert-butoxycarbonyl(2,4-dimethoxybenzyl)amino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxylate (example 1G, 5.32 g, 9.9 mmol) in ethanol (49.5 mL) was added 1 N NaOH aqueous solution (49.5 mL). The reaction mixture was heated at 60° C. 3 h and cooled to rt. Ethanol was removed by concentration in vacuo. The residue was acidified with 1 N HCl and the product was collected by vacuum filtration. 4-(tert-Butoxycarbonyl(2,4-dimethoxybenzyl)amino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxylic acid (4.3 g, 8.44 mmol, 85% yield over two steps) was isolated as a white solid after drying on the vacuum.

Workup

temperature3 h and cooled to rt
customEthanol was removed by concentration in vacuo
filtrationthe product was collected by vacuum filtration

Sources & evidence

ORD record: ord-ba119bd7b2e94470811e242cc499b0cf
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202881B2

Reaction notes

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