Hydrochloric Acid → 6-chloro-5-[6-(3-hydroxypyrrolidin-1-yl)-2-methoxypyridin-3-yl]-1H-indole-3-carboxylic acid

HRID 1054879Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13]C)=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[C:16]([O:27][CH3:28])=[N:17][C:18]([N:21]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22]2)=[CH:19][CH:20]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[C:16]([O:27][CH3:28])=[N:17][C:18]([N:21]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22]2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A vial was charged with methyl 6-chloro-5-[6-(3-hydroxypyrrolidin-1-yl)-2-methoxypyridin-3-yl]-1H-indole-3-carboxylate (52.5 mg, 0.130 mmol), NaOH aqueous (2 mL, 2M) and methanol (2 mL). The mixture was heated at 80° C. for 3 hrs. The mixture was cooled to room temperature and neutralized with conc. HCl aqueous to pH=6. The mixture was evaporated to dryness, and the resulting residue was purified through prep. HPLC to give the title compound (18.9 mg, 37.3%) as off-white solid.

Workup

customThe mixture was evaporated to dryness
customthe resulting residue was purified through prep

Sources & evidence

ORD record: ord-cb51e566e4d045d09314e62a5076f469
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394285B2

Reaction notes

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