Dichloromethane → HCID 178479715, compound

HRID 1878448Notes

Reaction equation

HRID 1878448 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([CH:19]=[C:20]([C:22]([NH:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[O:23])[N:21]=4)[CH:18]=3)[N:10]=[CH:9]2)C=CC=CC=1.[Cl:43]CCl>Cl.CO>[ClH:43].[NH:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([CH:19]=[C:20]([C:22]([NH:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:23])[N:21]=3)[CH:18]=2)[N:10]=[CH:9]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 687815006-(1-triphenylmethyl-1H-imidazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Product 1

HCID 178479715HCID 178479715, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 270 mg of 6-(1-triphenylmethyl-1H-imidazol-4-yl)-N-phenyl-imidazo[1,2-a]pyridine-2-carboxamide in 4 mL of 2N hydrochloric acid is heated for 30 minutes at 70° C. and then diluted with 2 mL of methanol, heated for 45 minutes at reflux, diluted again by addition of 2 mL of dichloromethane and heated for a further 2 hours at reflux. The reaction mixture is stirred for 60 hours at room temperature. The precipitate is filtered off by suction, washed with methanol, water and then pentane and dried under reduced pressure to give 96 mg of 6-(1H-imidazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide hydrochloride (1:1) in the form of a white solid.

Workup

  1. temperatureheated for 45 minutes
  2. temperatureat reflux
  3. temperatureheated for a further 2 hours
  4. temperatureat reflux
  5. filtrationThe precipitate is filtered off by suction
  6. washwashed with methanol, water
  7. dry with materialpentane and dried under reduced pressure

Sources & evidence

ORD record
ord-74b57102bd064c39b5259cfef699e276
Source dataset
uspto-grants-2012_11
Patent number
US08314109B2

Reaction notes

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