Dichloromethane → 1-(4-Ethylcyclohexyl)-3-(1-isobutyrylpiperidin-4-yl)urea

HRID 574688노트

반응식

HRID 574688 반응식
F[C:2](F)(F)[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:26])[CH:22]([CH3:25])[CH2:23]C)[CH2:17][CH2:16]1.[CH2:27](Cl)Cl>>[CH2:2]([CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:26])[CH:22]([CH3:25])[CH3:23])[CH2:17][CH2:16]2)=[O:11])[CH2:5][CH2:4]1)[CH3:27]

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 167829341-(4-Amino-1-piperidinyl)-2-methyl-1-butanone

생성물 1

HCID 716780091-(4-Ethylcyclohexyl)-3-(1-isobutyrylpiperidin-4-yl)urea수율 42%

실험 절차

4-(Trifluoromethyl)phenylisocyanate (100 mg, 0.65 mmol) and 1-(4-aminopiperidin-1-yl)-2-methylbutan-1-one (111 mg, 0.53 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 (89 mg, 2.76 mmol, 42%). H-NMR (DMSO-d6) ∂ 0.83 (t, J=8 Hz, 3H), 0.91 (m, 1H), 0.97 (m, 7H), 1.03 (m, 3H), 1.16 (m, 4H), 1.69 (m, 3H), 1.78 (m, 3H), 2.72 (t, J=12 Hz, 1H), 2.85 (m, 1H), 3.10 (t, J=12 Hz, 1H), 3.24 (m, 1H), 3.57 (m, 1H), 3.79 (d, J=13 Hz, 1H), 4.14 (d, J=13 Hz, 1H), 5.56 (d, J=7.5 Hz, 1H), 5.70 (d, J=7.5 Hz, 1H).

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-b897d4b10249411582059d8ed0368668
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034903B2

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