Diisopropylethylamine → HCID 58248008, 화합물

HRID 339133

반응식

HRID 339133 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](O)=[O:19])=[CH:12][C:11]=1[C:21]([F:24])([F:23])[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(O)C2N=NNC=2C=1.Cl.C(N=C=NCCCN(C)C)C.CCN(C(C)C)C(C)C.[F:57][C:58]([F:72])([F:71])[CH:59]([C:61]1[CH:66]=[CH:65][CH:64]=[C:63]([C:67]([F:70])([F:69])[F:68])[CH:62]=1)[NH2:60]>ClCCl>[O:19]=[C:18]([NH:60][CH:59]([C:61]1[CH:66]=[CH:65][CH:64]=[C:63]([C:67]([F:68])([F:69])[F:70])[CH:62]=1)[C:58]([F:71])([F:72])[F:57])/[CH:17]=[CH:16]/[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:11]([C:21]([F:22])([F:23])[F:24])[CH:12]=1

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 438251722,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethanamineHCID 58248002HCID 58248002, 화합물HCID 178516184HCID 178516184, 화합물

생성물 1

HCID 58248008HCID 58248008, 화합물수율 130.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 980 mg (1 eq, 2.84 mmol) of (2E)-3-[4-{[(tert-butoxycarbonyl)amino]methyl}-3-(trifluoromethyl)phenyl]acrylic acid in 10 ml of dichloromethane were added 481 mg (1 eq, 2.84 mmol) of 6-chlorohydroxybenzotriazole and 707 mg (1.3 eq, 3.70 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) and 733 mg (2 eq, 5.68 mmol, 989 μl) of Huenig's base. The reaction mixture was stirred at room temperature for 20 min. Then 1.04 g (1.5 eq, 4.26 mmol) of 2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanamine as a solution in 1 ml of CH2Cl2 were added, and the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and partitioned between saturated Na2CO3 solution and ethyl acetate. After drying and concentrating the solvent, 2.108 g of tert-butyl {4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzyl}carbamate were obtained as an oil, which was converted in the next step without further purification.

후처리

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between saturated Na2CO3 solution and ethyl acetate
  4. customAfter drying
  5. concentrationconcentrating the solvent

출처 및 근거

ORD 기록
ord-55855fea772f40799346b45cbe51438d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889878B2

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