Azetidine → [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl][1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone

HRID 72700Notes

Reaction equation

HRID 72700 reaction equation
Cl[C:2]1[C:7]([C:8]([C:10]2[CH:11]=[N:12][N:13]([CH3:22])[C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[O:9])=[C:6]([Cl:23])[N:5]=[CH:4][N:3]=1.[NH:24]1[CH2:27][CH2:26][CH2:25]1.C(N(CC)C(C)C)(C)C>C(#N)C>[N:24]1([C:2]2[C:7]([C:8]([C:10]3[CH:11]=[N:12][N:13]([CH3:22])[C:14]=3[C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)=[O:9])=[C:6]([Cl:23])[N:5]=[CH:4][N:3]=2)[CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 86712558(4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone

Product 1

HCID 86712559[4-(azetidin-1-yl)-6-chloropyrimidin-5-yl][1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone (C5) (200 mg, 0.576 mmol) in acetonitrile (6.0 mL) were added azetidine (39.0 μL, 0.576 mmol) and N,N-diisopropylethylamine (151 μL, 0.867 mmol). The reaction mixture was stirred at room temperature overnight and then concentrated in vacuo. The product was carried to Step 7 without further purification. LCMS m/z 368.4 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was carried to Step 7 without further purification

Sources & evidence

ORD record
ord-90c66d0931dc44a9b678c7fbd4d7f5a4
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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