Water → HCID 24988327, compound

HRID 216626Notes

Reaction equation

HRID 216626 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]([NH:11][C:12]1[NH:13][C:14]2[C:19]([C:20]=1[C:21]([NH2:23])=[O:22])=[CH:18][CH:17]=[C:16]([C:24]1[N:25](C(OC(C)(C)C)=O)[CH:26]=[CH:27][CH:28]=1)[CH:15]=2)=[O:10].[OH-].[Na+].O>ClCCl>[NH2:8][C:9]([NH:11][C:12]1[NH:13][C:14]2[C:19]([C:20]=1[C:21]([NH2:23])=[O:22])=[CH:18][CH:17]=[C:16]([C:24]1[NH:25][CH:26]=[CH:27][CH:28]=1)[CH:15]=2)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59189896HCID 59189896, compound2×

Product 1

HCID 24988327HCID 24988327, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.50 mL, 6.7 mmol) was added to a solution of 2-aminocarbonylamino-6-(1-tert-butoxycarbonylpyrrol-2-yl)indole-3-carboxamide (Compound 4-20, 28 mg, 0.073 mmol) in dichloromethane (0.5 mL) under ice-cooling, and the mixture was stirred for 30 minutes. 2 N Sodium hydroxide aqueous solution (3.5 mL) and water (10 mL) were added to the reaction mixture, and the whole was extracted with ethyl acetate (15 mL). The organic layer was washed with water (5 mL), brine (5 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (6.0 mg) as an off-white solid (yield 29%).

Workup

  1. temperaturecooling
  2. extractionthe whole was extracted with ethyl acetate (15 mL)
  3. washThe organic layer was washed with water (5 mL), brine (5 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-29680f525c8f4665ba38df72ffcf41de
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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