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Acetone → 4-[6-(1-Methylethyl)-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl]benzonitrile

HRID 1364160
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HRID 1364160 반응식
[N:1]1[N:2]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=12.[CH3:19][C:20]([CH3:22])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCl.C(O)(=O)C>[CH3:19][CH:20]([N:8]1[CH2:9][CH2:10][C:4]2=[CH:3][N:2]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[N:1]=[C:5]2[CH2:6][CH2:7]1)[CH3:22]
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참가 물질

7

반응물 4

HCID 180Acetone2회HCID 887MethanolHCID 5049666Sodium triacetoxyborohydride2회HCID 669308824-(5,6,7,8-Tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile

생성물 1

HCID 160489134-[6-(1-Methylethyl)-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl]benzonitrile

시약·촉매·용매 2

HCID 176
Acetic Acid
촉매
HCID 6344Dichloromethane용매

실험 절차

4-(5,6,7,8-Tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile (may be prepared as described in Description 11) (assumed 0.148 mmol) was dissolved in dichloromethane (2 ml) and acetic acid (2 drops). Acetone (16 μl, 0.22 mmol) and sodium triacetoxyborohydride (47 mg, 0.22 mmol) were added and the mixture stirred at room temperature for 2 hours. Further aliquots of acetone (32 μl, 0.44 mmol) and sodium triacetoxyborohydride (47 mg, 0.22 mmol) were added and stirring continued for a further 70 hours. Methanol was added and the solution poured onto a 2 g SCX column which was eluted with methanol then 2M ammonia in methanol. The basic fractions were evaporated and the residue purified by flash chromatography eluting with 0-5% 2M ammonia in methanol/dichloromethane to afford the title compound (E34).

후처리

  1. stirringstirring
  2. waitcontinued for a further 70 hours
  3. additionthe solution poured onto a 2 g SCX column which
  4. washwas eluted with methanol
  5. customThe basic fractions were evaporated
  6. customthe residue purified by flash chromatography
  7. washeluting with 0-5% 2M ammonia in methanol/dichloromethane

출처 및 근거

ORD 기록
ord-ec0486c7d65443618ed1c9457a79373e
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07888347B2

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