Acetonitrile → HCID 53312034, compound

HRID 1966995Notes

Reaction equation

HRID 1966995 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[N:17]([C:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[O:27][C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[Cl:35])=[O:20])[CH3:18])C)(C)(C)C.[OH-].[Na+].C(#N)C>Cl>[Cl:35][C:29]1[CH:30]=[CH:31][C:32]([Cl:34])=[CH:33][C:28]=1[O:27][C:26]1[C:21]([C:19]([N:17]([C:10]2[CH:11]=[C:12]([F:16])[C:13]([F:15])=[CH:14][C:9]=2[NH:7][CH3:6])[CH3:18])=[O:20])=[CH:22][N:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 67320582HCID 67320582, compound

Product 1

HCID 53312034HCID 53312034, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 100 mg (0.186 mmol) (2-{[4-(2,5-dichloro-phenoxy)-pyridine-3-carbonyl]-methyl-amino}-4,5-difluoro-phenyl)-methyl-carbamic acid tert-butyl ester in 1.5 mL 1M aqueous hydrochloric acid was stirred for 4 hours at 90° C. The reaction mixture was cooled down to room temperature and 2 mL 1M aqueous sodium hydroxide solution and 1 mL acetonitrile were added. The light yellow solution was directly purified by preparative HPLC (Phenomenex Gemini column) with a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2) to give 18 mg (22%) of the title compound as a colorless solid. MS (ESI): m/z=438.058 [M+H]+.

Workup

  1. customThe light yellow solution was directly purified by preparative HPLC (Phenomenex Gemini column) with a gradient of acetonitrile

Sources & evidence

ORD record
ord-2633fe578725430a903a64c0d582942a
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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