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

HRID 574688ノート

反応式

HRID 574688 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b897d4b10249411582059d8ed0368668
出典データセット
uspto-grants-2015_05
特許番号
US09034903B2

反応ノート

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