Cyclobutanone → 6-Cyclobutyl-2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

HRID 1364154노트

반응식

HRID 1364154 반응식
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:22]=[C:21]4[C:15]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)=[N:14]3)=[CH:9][CH:8]=2)[O:4][N:3]=1.[C:23]1(=O)[CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:23]1([N:18]2[CH2:19][CH2:20][C:21]3=[CH:22][N:13]([C:10]4[CH:11]=[CH:12][C:7]([C:5]5[O:4][N:3]=[C:2]([CH3:1])[N:6]=5)=[CH:8][CH:9]=4)[N:14]=[C:15]3[CH2:16][CH2:17]2)[CH2:26][CH2:25][CH2:24]1

참가 물질

7

반응물 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 669307922-[4-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

생성물 1

HCID 160488346-Cyclobutyl-2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (prepared as described in Description 35) (31 mg, 0.10 mmol) in dichloromethane (4 ml) was added cyclobutanone (30 mg, 0.42 mmol) and acetic acid (3 drops). The resulting mixture was stirred at room temperature, under argon, for 20 minutes. Sodium triacetoxyborohydride (89 mg, 0.42 mmol) was added and stirring continued overnight. The resulting crude mixture was diluted with methanol and then purified by SCX, eluting with methanol and then with 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo to afford the title compound (E25). MS (ES+) m/e 350 [M+H]+.

후처리

  1. stirringstirring continued overnight
  2. custompurified by SCX
  3. washeluting with methanol
  4. customsolvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-4d7b56e1bf104a6c957fe04ccc6b94c7
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888347B2

반응 노트

불러오는 중…