Iodoethane → HCID 16048761, compound

HRID 1364148Notes

Reaction equation

HRID 1364148 reaction equation
[N:1]1[N:2]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])=[CH:13][CH:12]=2)[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=12.C(=O)([O-])[O-].[K+].[K+].I[CH2:30][CH3:31]>C(O)C>[CH2:30]([N:8]1[CH2:9][CH2:10][C:4]2=[CH:3][N:2]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:21][CH2:20][CH2:19][C:18]4=[O:22])=[CH:15][CH:16]=3)[N:1]=[C:5]2[CH2:6][CH2:7]1)[CH3:31]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium Carbonate2×HCID 66930837HCID 66930837, compound

Product 1

HCID 16048761HCID 16048761, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1-[4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)phenyl]-2-pyrrolidinone (may be prepared as described in Description 22) (50 mg, 0.17 mmol) in ethanol (5 ml) was added potassium carbonate (70 mg, 0.51 mmol) and iodoethane (53 mg, 0.34 mmol). The resulting mixture was heated at reflux, under argon, for 18 hours. A further 3 eq. of potassium carbonate in ethanol (2 ml) was added, and stirring continued over the weekend. Reaction was removed from heat and ethanol (˜20 ml) was added. Reaction was purified by SCX, eluting with methanol and then with 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo. The resulting crude product was purified further by column chromatography on silica gel eluting with a mixture of methanol in dichloromethane (100:1-10:1) to afford the title compound (E18). MS (ES+) m/e 325 [M+H]+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux, under argon, for 18 hours
  3. customReaction
  4. customwas removed
  5. temperaturefrom heat
  6. additionethanol (˜20 ml) was added
  7. customReaction
  8. customwas purified by SCX
  9. washeluting with methanol
  10. customsolvent evaporated in vacuo
  11. customThe resulting crude product was purified further by column chromatography on silica gel eluting with a mixture of methanol in dichloromethane (100:1-10:1)

Sources & evidence

ORD record
ord-ca6a88127c9b4db9916f9d8db0a0efdc
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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