Triethylamine → HCID 17973675, compound

HRID 2077418Notes

Reaction equation

HRID 2077418 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:5]([C:7](Cl)=[O:8])[N:6]=1.[Br:17][C:18]1[C:26]2[N:25]=[C:24]([CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]3)[NH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl>[Br:17][C:18]1[C:26]2[N:25]=[C:24]([CH2:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][N:29]3[C:7]([C:5]3[N:6]=[C:2]([CH3:1])[S:3][C:4]=3[C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[O:8])[NH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 223241192-Methyl-5-(4-fluorophenyl)thiazole-4-carbonyl chlorideHCID 23146257HCID 23146257, compound

Product 1

HCID 17973675HCID 17973675, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-5-(4-fluorophenyl)thiazole-4-carbonyl chloride (383 mg, 1.5 mmol) was added portionwise over 5 min. to a stirred solution of (RS)-4-bromo-2-piperidin-2-ylmethyl-1H-benzoimidazole, D39 (400 mg, 1.4 mmol) and triethylamine (0.57 ml, 5.0 mmol) in dichloromethane (20 ml) at room temperature. After 20 h the mixture was washed with saturated sodium hydrogen carbonate. The organic layer was dried (Na2SO4) and the solvent removed in vacuo. Chromatography (silica gel, 10-100% ethyl acetate-hexane then 1-10% methanol-ethyl acetate) afforded the title compound as a pale brown amorphous solid (620 mg, 89%).

Workup

  1. washAfter 20 h the mixture was washed with saturated sodium hydrogen carbonate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-443aa5658ace4a19b672f983b42ced07
Source dataset
uspto-grants-2011_04
Patent number
US07928125B2

Reaction notes

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