Triethylamine → 4-(4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-[1,4]diazepan-1-ylmethyl)-benzoic acid

HRID 1509876Notes

Reaction equation

HRID 1509876 reaction equation
Cl.[N:2]1([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[N:19]=[C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:21][C:22]=3[C:23]([F:26])([F:25])[F:24])=[O:17])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=1.C(N(CC)CC)C>CN(C=O)C>[C:27]1([C:20]2[O:21][C:22]([C:23]([F:26])([F:24])[F:25])=[C:18]([C:16]([NH:15][C:12]3[CH:13]=[CH:14][C:9]([N:2]4[CH2:8][CH2:7][CH2:6][N:5]([CH2:34][C:35]5[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=5)[CH2:4][CH2:3]4)=[CH:10][CH:11]=3)=[O:17])[N:19]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 225994-(Bromomethyl)benzoic acidHCID 866388652-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-[1,4]diazepan-1-yl-phenyl)-amide hydrochloride

Product 1

HCID 591856734-(4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-[1,4]diazepan-1-ylmethyl)-benzoic acidYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-[1,4]diazepan-1-yl-phenyl)-amide hydrochloride (56 mg, 0.12 mmol), 4-bromomethyl-benzoic acid (28 mg, 0.13 mmol), triethylamine (0.07 mL, 0.50 mmol) in DMF (5 mL) was stirred at room temperature for 0.5 hr then concentrated and the residue was taken up in 50 mL of ethyl acetate and washed with 50 mL of saturated ammonium chloride, water (50 mL), and dried with anhydrous sodium sulfate. The solvent was removed and the residue was triturated with ethyl acetate, followed by filtration, to afford 4-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-[1,4]diazepan-1-ylmethyl)-benzoic acid as a yellow solid (20 mg, 29% yield) LCMS for C30H27F3N4O4 calcd. (m/e) 564, observed 565 (M+H).

Workup

  1. concentrationthen concentrated
  2. washwashed with 50 mL of saturated ammonium chloride, water (50 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed
  5. customthe residue was triturated with ethyl acetate
  6. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-a63c42eaf8e04591986615cc02146db7
Source dataset
uspto-grants-2012_07
Patent number
US08211884B2

Reaction notes

Loading…