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

HRID 1509876
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HRID 1509876 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a63c42eaf8e04591986615cc02146db7
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08211884B2

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