Potassium Carbonate → 5-[(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-2-cyclopentyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine

HRID 1713170Notes

Reaction equation

HRID 1713170 reaction equation
Cl.[CH:2]1([N:7]2[CH:15]=[C:10]3[CH2:11][NH:12][CH2:13][CH2:14][C:9]3=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([CH:26]2[CH2:29][CH2:28][CH2:27]2)[CH2:22][CH2:21]1)=[O:19].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:26]1([N:23]2[CH2:24][CH2:25][N:20]([C:18](=[O:19])[CH2:17][N:12]3[CH2:13][CH2:14][C:9]4=[N:8][N:7]([CH:2]5[CH2:6][CH2:5][CH2:4][CH2:3]5)[CH:15]=[C:10]4[CH2:11]3)[CH2:21][CH2:22]2)[CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazineHCID 574499462-cyclopentyl-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine hydrochloride

Product 1

HCID 574499475-[(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-2-cyclopentyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-cyclopentyl-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine hydrochloride (143 mg, 0.63 mmol), 1-(chloroacetyl)-4-cyclobutylpiperazine (136 mg, 0.63 mmol), K2CO3 (348 mg, 2.52 mmol) and KI (10 mg, 0.06 mmol) in CH3CN (10 ml) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (10 mL) and EtOAc (10 mL). The layers are separated and the aqueous layer is extracted with EtOAc (3×10 mL) and the combined extracts are washed with brine (20 mL), dried and evaporated. The resulting oil is purified by flash column with DCM/MeOH/NH4OH (100:5:0.5) to give the title compound as a light yellow solid. MS (M+1): 372.3; 1H NMR (δ, CDCl3): 7.10 (s, 1H), 4.51-4.60 (m, 1H), 3.64 (q, 4H), 3.54 (s, 2H), 3.36 (s, 2H), 2.77-2.83 (m, 4H), 2.64-2.74 (m, 1H), 2.25-2.32 (m, 4H), 1.62-2.62 (m, 14H).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (10 mL) and EtOAc (10 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (3×10 mL)
  5. washthe combined extracts are washed with brine (20 mL)
  6. customdried
  7. customevaporated
  8. customThe resulting oil is purified by flash column with DCM/MeOH/NH4OH (100:5:0.5)

Sources & evidence

ORD record
ord-6c1352e6788144e7b7a2358d336513cd
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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