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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
Notes
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Reaction equation

HRID 1713160 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fe56d12ec4344d7e85e3dc0fa343acf6
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795262B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes