4-Nitrophenyl chloroformate → 1-(5-tert-Butylisoxazol-3-yl)-3-(2-fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)urea

HRID 1807751

반응식

HRID 1807751 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:33].[C:34](Cl)(=O)[O:35]C1C=CC([N+]([O-])=O)=CC=1.[C:47]([C:51]1[O:55][N:54]=[C:53]([NH2:56])[CH:52]=1)([CH3:50])([CH3:49])[CH3:48]>O1CCCC1>[C:47]([C:51]1[O:55][N:54]=[C:53]([NH:56][C:34]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:24]([F:25])([F:26])[F:27])[C:28]([F:30])([F:31])[F:29])=[CH:19][CH:18]=4)[CH2:14][CH2:15]3)=[O:9])=[CH:4][C:3]=2[F:33])=[O:35])[CH:52]=1)([CH3:50])([CH3:49])[CH3:48]

참가 물질

5

반응물 3

HCID 821294-Nitrophenyl chloroformateHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 86638550(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone

생성물 1

HCID 445121541-(5-tert-Butylisoxazol-3-yl)-3-(2-fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)urea수율 5.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
120 °C

실험 절차

(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone (0.417 mmol, 0.2 g) and 4-nitrophenyl carbono-chloridate (0.417 mmol, 0.084 g) were combined and stirred in tetrahydrofuran (2 mL) at room temperature for 1 hour. 5-tert-Butylisoxazol-3-amine (1.252 mmol, 0.175 g) was added and the reaction heated in the microwave to 120° C. for 10 minutes. The solvent was removed at reduced pressure and the resulting residue purified by silica column chromatography (eluant dichloromethane/methanol 0% to 5%) to afford the title compound (14 mg). MS (ESI) m/z 646.5 [M+H]+

후처리

  1. customThe solvent was removed at reduced pressure
  2. customthe resulting residue purified by silica column chromatography (eluant dichloromethane/methanol 0% to 5%)

출처 및 근거

ORD 기록
ord-da286ada38ad4812941d8e9424fecd87
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357679B2

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