2,2,2-Trifluoroethylamine hydrochloride → 5-(3-Butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

HRID 1695458Notes

Reaction equation

HRID 1695458 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([C:18]([OH:20])=O)[N:15]([CH3:17])[N:16]=2)=[C:8]([CH2:21][OH:22])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.[F:55][C:56]([F:60])([F:59])[CH2:57][NH2:58]>CN(C=O)C>[F:55][C:56]([F:60])([F:59])[CH2:57][NH:58][C:18]([C:14]1[N:15]([CH3:17])[N:16]=[C:12]([O:11][CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH2:21][OH:22])[CH:13]=1)=[O:20]

Participants

6

Reactant 4

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666438885-(3-butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid

Product 1

HCID 497929605-(3-Butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid (2,2,2-trifluoro-ethyl)-amideYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(3-butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid (50 mg, 0.16 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (57 mg, 0.18 mmol), N,N-diisopropyl ethyl amine (138 μL, 0.8 mmol) and 2,2,2-trifluoroethylamine HCl (24 mg, 0.18 mmol). The resulting reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (silica, dichloromethane:methanol=100:0 to 95:5) afforded the title compound (47 mg, 75%) as a colorless oil. MS: m/e=391.2 [M+H]+.\

Workup

  1. customThe resulting reaction mixture
  2. concentrationConcentration and purification by chromatography (silica, dichloromethane:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-c8306cb80cea42e180d31ff40b78e462
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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