Potassium Carbonate → 6-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-5-methylpyridazin-3-amine

HRID 869161

Reaction equation

HRID 869161 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][NH2:10])=[CH:4][CH:3]=1.[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][C:19]=1[CH3:20].C([O-])([O-])=O.[K+].[K+]>C(O)(C)C>[Cl:13][C:14]1[N:15]=[N:16][C:17]([NH:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)([CH3:12])[CH3:11])=[CH:18][C:19]=1[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 879233,6-Dichloro-4-methylpyridazineHCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amine

Product 1

HCID 866861326-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-5-methylpyridazin-3-amineYield 15.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (2-(4-fluorophenyl)-2-methylpropan-1-amine (5.5 g, 33 mmol, 1.8 equiv), 3,6-dichloro-4-methylpyridazine (3.0 g, 18 mmol, 1.0 equiv) and K2CO3 (5.1 g, 37 mmol, 2.0 equiv) in isopropanol (7.5 mL) was stirred at 100° C. under a blanket of nitrogen for 18 hours. The cooled mixture was partitioned between water and EtOAc and the organic fraction was concentrated in vacuo. Purification over silica gel using a 20-35% gradient of EtOAc/hexanes gave the desired product (0.80 g, 15%) of a yellow oil which was determined by HPLC to be a 5:1 mixture of regioisomers by HPLC.

Workup

  1. customThe cooled mixture was partitioned between water and EtOAc
  2. concentrationthe organic fraction was concentrated in vacuo
  3. customPurification over silica gel using a 20-35% gradient of EtOAc/hexanes

Sources & evidence

ORD record
ord-a80060bc82a040bb876008e789711443
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Linked notes

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