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

HRID 1713170노트

반응식

HRID 1713170 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6c1352e6788144e7b7a2358d336513cd
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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