Acetyl chloride → HCID 178474645, compound

HRID 241462Notes

Reaction equation

HRID 241462 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:12]([NH:14][C:15]2[NH:16][C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[C:18]([CH3:20])[N:19]=2)=[O:13])[C:6]([CH:9]([F:11])[F:10])=[N:7][CH:8]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39].[NH4+].[Cl-]>C(Cl)Cl>[C:38]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:12]([NH:14][C:15]2[NH:16][C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[C:18]([CH3:20])[N:19]=2)=[O:13])[C:6]([CH:9]([F:11])[F:10])=[N:7][CH:8]=1)(=[O:40])[CH3:39]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 178433214HCID 178433214, compound

Product 1

HCID 178474645HCID 178474645, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 5-(aminomethyl)-2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide (0.047 g, 0.110 mmol) in DCM (3 mL). Add triethylamine (0.038 mL, 0.276 mmol) followed by acetyl chloride (9.830 μL, 0.138 mmol), and stir overnight. Pour the reaction into saturated aqueous NH4Cl (15 mL) solution, and extract with EtOAc (2×10 mL). Combine the organic extracts; dry the organic extracts over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to dryness to give the title compound (0.039 g, 75% yield) as a light yellow solid. LCMS (m/z) 468 (M+1).

Workup

  1. additionPour
  2. extractionextract with EtOAc (2×10 mL)
  3. dry with materialdry the organic extracts over sodium sulfate
  4. filtrationfilter
  5. customcollect the filtrate
  6. concentrationand concentrate the filtrate under reduced pressure to dryness

Sources & evidence

ORD record
ord-2dcf3f68f7204c90a267969d44159b09
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

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