Triethylamine → 5-{1-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester

HRID 30233

반응식

HRID 30233 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([OH:12])=O)=[CH:8][CH:9]=1)=[O:4].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[F:43][C:44]([F:64])([F:63])[O:45][C:46]1[CH:62]=[CH:61][C:49]([CH2:50][O:51][C:52]2[CH:57]=[CH:56][C:55]([CH:58]([NH2:60])[CH3:59])=[CH:54][CH:53]=2)=[CH:48][CH:47]=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:12])[NH:60][CH:58]([C:55]2[CH:56]=[CH:57][C:52]([O:51][CH2:50][C:49]3[CH:61]=[CH:62][C:46]([O:45][C:44]([F:43])([F:63])[F:64])=[CH:47][CH:48]=3)=[CH:53][CH:54]=2)[CH3:59])=[CH:8][CH:9]=1)=[O:4]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 8183525-(Methoxycarbonyl)thiophene-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 586290281-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylamine

생성물 1

HCID 691351185-{1-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester수율 60.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 160.0 mg (0.859 mmol) thiophene-2,5-dicarboxylic acid monomethyl ester in 25 ml dichloromethane were added 253.0 mg (1.293 mmol) N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, 175 mg (1.295 mmol) 1-hydroxybenzotriazole hydrate and 130.7 g (1.291 mmol) triethylamine. After 30 min at room temperature 268.0 mg (0.861 mmol) 1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethylamine were added. The reaction mixture was stirred for 6.5 h. The solvent was evaporated, to the residue was added ethyl acetate and the organic phase was extracted with saturated aqueous NaHCO3 solution and with water. The organic phase was dried over MgSO4 and the solvent was evaporated. The residue was triturated with diisopropyl to provide 249 mg (0.519 mmol) 5-{1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester.

후처리

  1. customThe solvent was evaporated, to the residue
  2. additionwas added ethyl acetate
  3. extractionthe organic phase was extracted with saturated aqueous NaHCO3 solution and with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent was evaporated
  6. customThe residue was triturated with diisopropyl

출처 및 근거

ORD 기록
ord-63ef497a63904ac69e93e587cc306d69
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423060B2

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