p-(Trifluoromethoxy)phenyl isocyanate → 1-(1-(2-Methylbutanoyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea

HRID 574687노트

반응식

HRID 574687 반응식
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:27])[CH:23]([CH3:26])[CH2:24][CH3:25])[CH2:18][CH2:17]1>C(Cl)Cl>[CH3:26][CH:23]([CH2:24][CH3:25])[C:22]([N:19]1[CH2:18][CH2:17][CH:16]([NH:15][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=2)=[O:12])[CH2:21][CH2:20]1)=[O:27]

참가 물질

4

반응물 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 167829341-(4-Amino-1-piperidinyl)-2-methyl-1-butanone

생성물 1

HCID 716801971-(1-(2-Methylbutanoyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea수율 895.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-(Trifluoromethoxy)phenylisocyanate (100 mg, 0.49 mmol) and 1-(4-aminopiperidin-1-yl)-2-methylbutan-1-one (90 mg, 0.49 mmol) was dissolved in CH2Cl2 (100 mL) and stirred for 12 h. The reaction was quenched by addition of water. The organic layer was isolated and the aqueous layer was extracted with EtOAc for 4 times. The combined organic layer was concentrated under vacuo and was further purified by flash chromatography (EtOAc:Hex/1:1) yielding final product (168 mg, 4.39 mmol, 89%). H-NMR (DMSO-d6) ∂ 0.80 (m, 3H), 0.97 (m, 3H), 1.28 (m, 3H), 1.53 (m, 1H), 1.85 (tbr, 2H), 2.71 (m, 1H), 2.78 (m, 1H), 3.16 (t, J=12 Hz, 1H), 3.71 (m, 1H), 3.88 (d, J=12 Hz, 1H), 4.21 (br, 1H), 6.26 (tbr, 1H), 7.22 (d, J=9 Hz, 2H), 7.47 (d, J=9 Hz, 2H), 8.55 (d, J=9 Hz, 2H).

후처리

  1. customThe reaction was quenched by addition of water
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was extracted with EtOAc for 4 times
  4. concentrationThe combined organic layer was concentrated under vacuo
  5. customwas further purified by flash chromatography (EtOAc:Hex/1:1)

출처 및 근거

ORD 기록
ord-25852ef2c42d4877aea51b13bd09e158
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034903B2

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