2-[4-(5-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-1-phenyl-ethylamine → [4-(5-Methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-acetonitrile

HRID 45513Notes

Reaction equation

HRID 45513 reaction equation
C([Mg]Br)C1C=CC=CC=1.C1([Mg]Br)C=CC=CC=1.C([CH:25]([NH2:43])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[C:34]([C:39]([F:42])([F:41])[F:40])=[N:35][NH:36][C:37]=2[CH3:38])=[CH:29][CH:28]=1)C1C=CC=CC=1.CC1NN=C(C(F)(F)F)C=1C1C=CC(CC(N)C2C=CC=CC=2)=CC=1>>[CH3:38][C:37]1[NH:36][N:35]=[C:34]([C:39]([F:42])([F:41])[F:40])[C:33]=1[C:30]1[CH:31]=[CH:32][C:27]([CH2:26][C:25]#[N:43])=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 672347712-[4-(5-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-1-phenyl-ethylamineHCID 672362211-benzyl-2-[4-(5-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-ethylamineHCID 178418255HCID 178418255, compoundHCID 178419663HCID 178419663, compound

Product 1

HCID 59331945[4-(5-Methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-acetonitrile

Procedure

The product of Example 37B can also be reacted with benzyl magnesium bromide or phenyl magnesium bromide under the Grignard reaction conditions described in Example 5 to give (following deprotection by the method of Example 37C) 1-benzyl-2-[4-(5-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-ethylamine and 2-[4-(5-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-phenyl]-1-phenyl-ethylamine respectively.

Workup

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Sources & evidence

ORD record
ord-ba2091e6a05344179edc76efdd76a545
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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