HCID 22031010, compound → HCID 178484453, compound

HRID 1792604Notes

Reaction equation

HRID 1792604 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:20]=[CH:19][N:18]([C:21]5[CH:31]=[CH:30][C:24]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])=[CH:23][N:22]=5)[C:17]=4[CH:32]=3)=[CH:11][N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[CH:4][CH:3]=1>O1CCCC1.CO.Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:20]=[CH:19][N:18]([C:21]5[CH:31]=[CH:30][C:24]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])=[CH:23][N:22]=5)[C:17]=4[CH:32]=3)=[CH:11][NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 22031010HCID 22031010, compound

Product 1

HCID 178484453HCID 178484453, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

43 mg 6-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-1H-benzo[d]imidazol-1-yl}-N,N-dimethyl-nicotinamide (compound in Example 716) was dissolved in 8.0 mL solvent mixture of tetrahydrofuran and methanol (1:1), 3.0 mL of 5 N hydrochloric acid was added thereto, and the mixture was left at room temperature for 3 hours. The reaction solution was neutralized and then extracted with ethyl acetate. The extract was purified by silica gel column chromatography (ethyl acetate/methanol) and recrystallized from methanol/diethyl ether, to give 24 mg of the title compound as colorless crystals.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. customThe extract was purified by silica gel column chromatography (ethyl acetate/methanol)
  4. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-d806ae520a0e4e56b86e054851d65370
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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