Water → HCID 59285869, compound

HRID 1011574Notes

Reaction equation

HRID 1011574 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]#[N:29].O>CN(C)C=O>[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:27][C:28]#[N:29])=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 59285839HCID 59285839, compound

Product 1

HCID 59285869HCID 59285869, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2-aminocarbonylamino-5-(2-hydroxyphenyl)pyrrole-3-carboxamide (Compound No. 3-1, 52 mg, 0.20 mmol), potassium carbonate (43 mg, 0.31 mmol), bromoacetonitrile (15 μL, 0.22 mmol) in anhydrous N,N-dimethylformamide (1 mL) was stirred at 60° C. for 2.5 hours. After cooling to room temperature, water (10 mL) was added thereto and the precipitated solid was filtered off. The obtained solid was dried under reduced pressure to give the target compound (32 mg) as a pale brown solid (Yield 54%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitated solid was filtered off
  3. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-1c0dd6d311e8498f94f82a15d772a4ac
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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