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

HRID 1364152Notes

Reaction equation

HRID 1364152 reaction equation
[N:1]1[N:2]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O: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:20]1(=O)[CH2:24][CH2:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCl.C(O)(=O)C>[CH:20]1([N:8]2[CH2:9][CH2:10][C:4]3=[CH:3][N:2]([C:11]4[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=4)[N:1]=[C:5]3[CH2:6][CH2:7]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8452Cyclopentanone2×HCID 5049666Sodium triacetoxyborohydrideHCID 66930841HCID 66930841, compound

Product 1

HCID 160488324-(6-Cyclopentyl-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide (may be prepared as described in Description 37) (31 mg, 0.12 mmol) in dichloromethane (3 ml) was added cyclopentanone (20 mg, 0.24 mmol) and acetic acid (2 drops). The resulting mixture was stirred at room temperature, under argon, for 20 minutes. Sodium triacetoxyborohydride (51 mg, 0.24 mmol) was added and stirring continued for 2 hours. A further 6 eq. of cyclopentanone was added and stirring continued over the weekend. Methanol was added and the crude mixture was 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 (E23). MS (ES+) m/e 325 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. stirringstirring
  4. customthe crude mixture was purified by SCX
  5. washeluting with methanol
  6. customsolvent evaporated in vacuo

Sources & evidence

ORD record
ord-1fcefaa3fa27454fb14b092124e04935
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

Loading…