1-Hydroxybenzotriazole → 2-(4-(1-(tert-butyldimethylsilyloxy)-cyclopropyl)-3-fluorophenyl)-N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide

HRID 1842904노트

반응식

HRID 1842904 반응식
[Si:1]([O:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:22])[C:19]([OH:21])=O)=[CH:14][C:13]=2[F:23])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[Cl:55][C:56]1[CH:57]=[C:58]([N:62]2[C:66]([CH2:67][NH2:68])=[CH:65][C:64]([C:69]([F:72])([F:71])[F:70])=[N:63]2)[CH:59]=[CH:60][CH:61]=1>C(Cl)Cl>[Si:1]([O:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:22])[C:19]([NH:68][CH2:67][C:66]3[N:62]([C:58]4[CH:59]=[CH:60][CH:61]=[C:56]([Cl:55])[CH:57]=4)[N:63]=[C:64]([C:69]([F:72])([F:71])[F:70])[CH:65]=3)=[O:21])=[CH:14][C:13]=2[F:23])[CH2:10][CH2:11]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

참가 물질

7

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66644230(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamineHCID 708164012-(4-(1-(Tert-butyldimethylsilyloxy)cyclopropyl)-3-fluorophenyl)propanoic acid

생성물 1

HCID 708159202-(4-(1-(tert-butyldimethylsilyloxy)-cyclopropyl)-3-fluorophenyl)-N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide수율 31%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-(4-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-3-fluorophenyl)propanoic acid (190 mg, 0.56 mmol, 1 eq) in DCM (10 mL) was added DIPEA (0.29 mL, 1.68 mmol, 3 eq) followed by EDC.HCl (128 mg, 0.67 mmol, 1.2 eq) and HOBt (103 mg, 0.67 mmol, 1.2 eq) at RT and stirred for 10 min when (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine (175 mg, 0.56 mmol) was added and the mixture stirred for 3 h. After completion of the reaction the reaction mixture was washed with H2O (15 mL), brine (10 mL), dried (Na2SO4) and the solvents evaporated. The crude product was purified by CC using EtOAc/PE (3:7) to get 2-(4-(1-(tert-butyldimethylsilyloxy)-cyclopropyl)-3-fluorophenyl)-N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide (103 mg; 31%) as off white solid (TLC system: EtOAc/PE (3:7) Rf: 0.5).

후처리

  1. additionwas added
  2. customAfter completion of the reaction the reaction mixture
  3. washwas washed with H2O (15 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe solvents evaporated
  6. customThe crude product was purified by CC

출처 및 근거

ORD 기록
ord-f288688769704c53b9e94b62741cede3
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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