Diisopropylethylamine → 6-Chloro-3-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazine-4-carboxamide

HRID 869164Notes

Reaction equation

HRID 869164 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:4][C:3]=1C.ClC1N=NC(Cl)=CC=1[C:28]([NH2:30])=[O:29].FC1C=CC(C(C)(C)CN)=CC=1.C(N(C(C)C)CC)(C)C>CC#N>[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)([CH3:11])[CH3:12])=[C:4]([C:28]([NH2:30])=[O:29])[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2620493,6-Dichloropyridazine-4-carboxamideHCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amineHCID 866861326-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-5-methylpyridazin-3-amine

Product 1

HCID 866861336-Chloro-3-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazine-4-carboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using a similar procedure as was used for 6-chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-5-methylpyridazin-3-amine in example 14, 3,6-dichloropyridazine-4-carboxamide (2.6 g, 13 mmol, 1.0 equiv), (2-(4-fluorophenyl)-2-methylpropan-1-amine (2.5 g, 15 mmol, 1.1 equiv), and diisopropylethylamine (2.8 mL, 16 mmol, 1.2 equiv) in CH3CN (54 mL) was heated at 60-90° C. for 48 hours. The product was purified over silica gel with 100% EtOAc to give the desired product (3.4 g, 78%) as a yellow foamy solid.

Workup

  1. customThe product was purified over silica gel with 100% EtOAc

Sources & evidence

ORD record
ord-9775c6bde164473aa93b86c9935c1de6
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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