Methanol → 3-((7-cyano-1-cyclopentyl-4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)amino)benzoic acid

HRID 2206179Notes

Reaction equation

[C:1]([C:3]1[C:4]2[N:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:12]=[C:11]([NH:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([O:25]C)=[O:24])[C:5]=2[C:6]([O:9][CH3:10])=[N:7][CH:8]=1)#[N:2].CO.C1COCC1.[OH-].[Na+]>O>[C:1]([C:3]1[C:4]2[N:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:12]=[C:11]([NH:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([OH:25])=[O:24])[C:5]=2[C:6]([O:9][CH3:10])=[N:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of methyl 3-((7-cyano-1-cyclopentyl-4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)amino)benzoate (90 mg) in a mixed solvent of methanol (1 mL) and THF (1 mL) was added 8N aqueous sodium hydroxide solution (0.288 mL), and the mixture was stirred at 80° C. for 4 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The aqueous layer was neutralized with 1N hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (80 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
customwas neutralized with 1N hydrochloric acid at 0° C.
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-06f1b07ca2b2456c9cc11d3e2341624e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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