Hydrochloric Acid → 1-(4-Fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)cyclohexanecarboxylic acid

HRID 530878Notes

Reaction equation

[OH-].[Na+].O.[F:4][C:5]1[CH:40]=[CH:39][C:8]([CH2:9][C:10]2([C:35]([O:37]C)=[O:36])[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][N:23]=[C:22]4[C:28]3[CH:33]=[CH:32][N:31]=[C:30]([CH3:34])[CH:29]=3)=[O:18])[CH2:11]2)=[CH:7][CH:6]=1.Cl>CO.C1COCC1>[F:4][C:5]1[CH:40]=[CH:39][C:8]([CH2:9][C:10]2([C:35]([OH:37])=[O:36])[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][N:23]=[C:22]4[C:28]3[CH:33]=[CH:32][N:31]=[C:30]([CH3:34])[CH:29]=3)=[O:18])[CH2:11]2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium hydroxide in water (4 M solution, 1 ml, 4 mmol) was added into a solution of methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)cyclohexanecarboxylate (0.32 mmol) in methanol (0.5 ml) and THF (2 ml). The reaction solution was stirred at 70° C. for 16 h, and 1.0 N HCl solution was added dropwise to adjust pH to 4. The resulting solution was extracted with EtOAc (10 ml, twice). The combined organic layers were dried over sodium sulfate, filtered, concentrated, and purified using HPLC to give the titled compound. LC-MS: 487.21 [M+11]. LC/MS RT=2.36 min.

Workup

extractionThe resulting solution was extracted with EtOAc (10 ml
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-7f68234ec90c4a798f79aac5422ad36c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09351965B2

Reaction notes

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