Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-(4-Fluoro-3-nitro-benzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

HRID 1410223Notes

Reaction equation

HRID 1410223 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[F:14][C:15]([F:23])([F:22])[C:16]1([C:19](O)=[O:20])[CH2:18][CH2:17]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:19]([C:16]2([C:15]([F:23])([F:22])[F:14])[CH2:18][CH2:17]2)=[O:20])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 53408003(4-Fluoro-3-nitrophenyl)methanamine hydrochloride

Product 1

HCID 59529826N-(4-Fluoro-3-nitro-benzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sub-title compound was prepared in accordance with the procedure in Example 72, step (c) using (4-fluoro-3-nitrophenyl)methylamine hydrochloride (3.0 g; 14.5 mmol), 1-(trifluoromethyl)-cyclopropanecarboxylic acid (2.5 g; 16.0 mmol), HBTU (6.07 g; 16.0 mmol), TEA (5.88 g; 58.1 mmol) and DMF (50 mL). Yield: 3.8 g (85%).

Sources & evidence

ORD record
ord-56f6b0d9dd9e410ab19bf4291ef16083
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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