Diisopropylethylamine → 3-[(4-Chlorophenyl)(3-{2-fluoro-1-[3-fluoro-5-(4H-1,2,4-triazol-4-yl)phenyl]-2-methylpropyl}azetidin-1-yl)methyl]benzonitrile

HRID 1724224Notes

Reaction equation

HRID 1724224 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([CH:6]([C:11]2[CH:12]=[C:13]([N:18]3[CH:22]=[N:21][N:20]=[CH:19]3)[CH:14]=[C:15]([F:17])[CH:16]=2)[C:7]([F:10])([CH3:9])[CH3:8])[CH2:3]1.Br[CH:24]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[C:28]#[N:29].C(N(C(C)C)CC)(C)C>CC#N>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([CH:24]([N:2]2[CH2:3][CH:4]([CH:6]([C:11]3[CH:12]=[C:13]([N:18]4[CH:19]=[N:20][N:21]=[CH:22]4)[CH:14]=[C:15]([F:17])[CH:16]=3)[C:7]([F:10])([CH3:9])[CH3:8])[CH2:5]2)[C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]#[N:29])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 670553513-[Bromo(4-chlorophenyl)methyl]benzonitrileHCID 67065977HCID 67065977, compound

Product 1

HCID 114209993-[(4-Chlorophenyl)(3-{2-fluoro-1-[3-fluoro-5-(4H-1,2,4-triazol-4-yl)phenyl]-2-methylpropyl}azetidin-1-yl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A sample of 135 mg (0.41 mmole) of 4-[3-(1-Azetidin-3-yl-2-fluoro-2-methylpropyl)-5-fluorophenyl]-4H-1,2,4-triazole hydrochloride, 211 mg (0.62 mmole) of 3-[bromo(4-chlorophenyl)methyl]benzonitrile and 181 uL (1.025 mmole) of diisopropylethylamine in 5 mL of dry CH3CN was heated at reflux for 3 h.

Workup

  1. temperatureat reflux for 3 h.

Sources & evidence

ORD record
ord-57bd896e7de84a6d9440e9e02aa4f6ff
Source dataset
uspto-grants-2009_02
Patent number
US07485732B2

Reaction notes

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