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

HRID 1713170ノート

反応式

HRID 1713170 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6c1352e6788144e7b7a2358d336513cd
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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