Triethylamine → 4-Phenylbutyl 2-(N-cyclohexylcarbamoyl)-perhydropyridazinecarboxylate

HRID 851942노트

반응식

HRID 851942 반응식
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[NH:11]1.C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([NH:7][C:8]([N:11]2[CH:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:17])[CH2:13][CH2:14][CH2:15][NH:10]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 184700714-Phenylbutyl perhydropyridazinecarboxylate

생성물 1

HCID 184700744-Phenylbutyl 2-(N-cyclohexylcarbamoyl)-perhydropyridazinecarboxylate수율 89.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Cyclohexylisocyanate (0.38 g, 3.0 mmol) was added to a CH2Cl2 solution containing 4-phenylbutyl perhydropyridazinecarboxylate (0.72 g, 2.75 mmol) and triethylamine (0.42 ml, 3 mmol). The reaction was stirred overnight at room temperature under nitrogen atmosphere, and then diluted to 50 ml CH2Cl2. The organic layer was washed with water, dried, and concentrated. The crude material was purified by silica gel column to yield 0.95 g (89%) final product as clear oil. Rf=0.28 (2:1 hexane:EtOAc). 1H NMR (CDCl3, 400 MHz): δ 1.10 (m, 3H); 1.33 (m, 3H); 1.69 (m, 10H); 1.88 (m, 2H); 2.62 (m, 2H); 2.72 (m, 1H); 2.87 (m, 1H); 3.60 (m, 1H); 4.13 (m, 3H); 4.38 (m, 1H); 5.11 (d, 1H, J=8.3); 7.23 (m, 5H). Anal. Calcd. for C22H28N3O3-0.14H2O: C, 67.75; H, 8.60; N, 10.77. Found: C, 67.75; H, 8.45; N, 10.90.

후처리

  1. washThe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel column

출처 및 근거

ORD 기록
ord-6a403b07fb864c96afab426ab9fad963
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253169B2

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