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

HRID 1713160
ノート
印刷プレビュー

反応式

HRID 1713160 の反応式
Cl.[Cl:2][C:3]1[N:8]=[N:7][C:6]([N:9]2[C:17]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]=3[CH:11]=[N:10]2)=[CH:5][CH:4]=1.Cl[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([CH:28]2[CH2:31][CH2:30][CH2:29]2)[CH2:24][CH2:23]1)=[O:21].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:2][C:3]1[N:8]=[N:7][C:6]([N:9]2[C:17]3[CH2:16][CH2:15][N:14]([CH2:19][C:20]([N:22]4[CH2:27][CH2:26][N:25]([CH:28]5[CH2:31][CH2:30][CH2:29]5)[CH2:24][CH2:23]4)=[O:21])[CH2:13][C:12]=3[CH:11]=[N:10]2)=[CH:5][CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazineHCID 866154151-(6-chloropyridazin-3-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine hydrochloride

生成物 1

HCID 574205871-(6-chloropyridazin-3-yl)-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

A mixture of 1-(6-chloropyridazin-3-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine hydrochloride (1.05 g, 3.86 mmol), 1-(chloroacetyl)-4-cyclobutylpiperazine (840 mg, 3.86 mmol), K2CO3 (2.11 g, 15.4 mmol) and KI (66 mg, 0.4 mmol) in CH3CN (20 mL) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (20 mL) and EtOAc (20 mL). The layers are separated and the aqueous layer is extracted with EtOAc (3×20 mL). The combined extracts are washed with brine (30 μL), dried and evaporated. The resultant oil is purified by flash column with DCM/MeOH/NH4OH (100:5:0.5) to give the title compound as a light yellow solid. 1H NMR (6, CDCl3): 8.16 (d, 1H), 7.57 (d, 1H), 7.51 (s, 1H), 3.58-3.62 (m, 6H), 3.40 (s, 2H), 3.35 (t, 2H), 2.86 (t, 2H), 2.62-2.72 (m, 1H), 2.27 (q, 4H), 1.62-2.02 (m, 6H). MS (M+1): 416.2.

後処理

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (20 mL) and EtOAc (20 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (3×20 mL)
  5. washThe combined extracts are washed with brine (30 μL)
  6. customdried
  7. customevaporated
  8. customThe resultant 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-fe56d12ec4344d7e85e3dc0fa343acf6
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07795262B2

反応ノート

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