Dichloromethane → HCID 44609726, compound

HRID 2094209Notes

Reaction equation

HRID 2094209 reaction equation
N([O-])=O.[Na+].[NH2:5][C:6]([NH:8][C:9]1[NH:10][C:11]2[C:16]([C:17]=1[C:18]([NH2:20])=[O:19])=[CH:15][CH:14]=[C:13]([O:21][C:22]1[CH:27]=[CH:26][C:25](N)=[CH:24][CH:23]=1)[CH:12]=2)=[O:7].[Cl:29]CCl>O.Cl.CO.[Cu]Cl>[NH2:5][C:6]([NH:8][C:9]1[NH:10][C:11]2[C:16]([C:17]=1[C:18]([NH2:20])=[O:19])=[CH:15][CH:14]=[C:13]([O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:29])=[CH:24][CH:23]=1)[CH:12]=2)=[O:7]

Participants

8

Reactant 3

HCID 6344DichloromethaneHCID 23668193Sodium NitriteHCID 67071861HCID 67071861, compound

Product 1

HCID 44609726HCID 44609726, compoundYield 8%

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Under ice-cooling, a solution of sodium nitrite (42 mg, 0.61 mmol) in water (400 μL) was added to a suspension of 2-aminocarbonylamino-6-(4-aminophenyloxy) indole-3-carboxamide (Compound No.5-1, 99 mg, 0.30 mmol) in anhydrous dichloromethane (2 mL) and 6N hydrochloric acid (4 mL) and the mixture was stirred for 2 hours. Moreover a solution of copper(I) chloride (162 mg, 1.6 mmol) in concentrated hydrochloric acid (500 μL) was added thereto and the mixture was stirred 30 minutes. The whole was stirred overnight at room temperature. The reaction solution was diluted with water (30 mL) and methanol (20 mL), extracted with ethyl acetate (100 mL). The organic layer was washed with brine (100 mL) and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography to give the title compound (9 mg) as a brown solid (8%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred 30 minutes
  3. stirringThe whole was stirred overnight at room temperature
  4. extractionextracted with ethyl acetate (100 mL)
  5. washThe organic layer was washed with brine (100 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter the solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dce0787e7fb3401bb811914494007cd6
Source dataset
uspto-grants-2013_05
Patent number
US08445529B2

Reaction notes

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