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

HRID 1364159Notes

Reaction equation

HRID 1364159 reaction equation
[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.[C:19]1(=O)[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCl.C(O)(=O)C>[CH:19]1([N:8]2[CH2:9][CH2:10][C:4]3=[CH:3][N:2]([C:11]4[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=4)[N:1]=[C:5]3[CH2:6][CH2:7]2)[CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 887MethanolHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 669308824-(5,6,7,8-Tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile

Product 1

HCID 160489114-(6-Cyclobutyl-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

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). Cyclobutanone (17 μl, 0.22 mmol) and sodium triacetoxyborohydride (47 mg, 0.22 mmol) were added and the mixture stirred at room temperature for 1 hour. 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 give the title compound (E32).

Workup

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

Sources & evidence

ORD record
ord-ffbfa2d8004d4afda1c853efcbbfd7bc
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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