Cyclobutylamine → HCID 54372919, 화합물

HRID 1734660노트

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HRID 1734660 반응식
C([O:4][CH:5]1[CH:9]([N:10]2[C:14]3[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:13]=3[N:12]=[C:11]2Br)[CH2:8][CH:7]([CH2:22][O:23]C(=O)C)[CH:6]1[O:27]C(=O)C)(=O)C.[CH:31]1([NH2:35])[CH2:34][CH2:33][CH2:32]1>C(O)C>[Cl:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]2[N:10]([CH:9]3[CH:5]([OH:4])[CH:6]([OH:27])[CH:7]([CH2:22][OH:23])[CH2:8]3)[C:11]([NH:35][CH:31]3[CH2:34][CH2:33][CH2:32]3)=[N:12][C:13]=2[CH:18]=1

참가 물질

4

반응물 2

HCID 75645CyclobutylamineHCID 54404171HCID 54404171, 화합물

생성물 1

HCID 54372919HCID 54372919, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

(±)(1R*, 2S*, 3S*, 5S*)-3-(Acetoxymethyl)-5-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (500 mg, 0.958 mmol) was dissolved in absolute ethanol (7 mL) and cyclobutylamine (0.41 mL, 4.8 mmol) was added. The solution was refluxed under nitrogen for 18 hours. Volatiles were evaporated and the residue stirred in methanol half-saturated with ammonia at 0° C. (20 mL) for 18 hours. Volatiles were removed in vacuo and the residue crystallized from ethanol-water to give title compound as white solid, m.p. 250° C. dec.; 1H-NMR(DMSO-d6)δ: 7.61 and 7.38 (both s, 1 each, aromatic CH), 7.07 (d, J=7.4 Hz, 1, NH), 5.15 (t, J=3.9 Hz, 1, OH), 4.81 (d, J=7.3 Hz, 1, OH), 4.71-4.45 (m overlapping d at 4.71, J=3.5 Hz, total 2, OH and NCH), 4.40-4.30 (m, 2. OCH and NCH), 3.82-3.80 (m, 1, OCH), 3.72-3.42 (both m, 1 each, OCH2), 2.32-1.67 (three m, 9, 4CH2 and CH); mass spectrum (CI): 386(M +1).

후처리

  1. temperatureThe solution was refluxed under nitrogen for 18 hours
  2. customVolatiles were evaporated
  3. customVolatiles were removed in vacuo
  4. customthe residue crystallized from ethanol-water

출처 및 근거

ORD 기록
ord-515c5540ef39402aace7ce5b2a41928a
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534535

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