Methanol → HCID 16048835, compound

HRID 1364155Notes

Reaction equation

HRID 1364155 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)[CH2:23][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)[CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 887MethanolHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 66930841HCID 66930841, compound

Product 1

HCID 16048835HCID 16048835, compound

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 cyclobutanone (17 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. 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 (E26). MS (ES+) m/e 311 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-a0071a9d7fde45e6bb4aa29e18665181
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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