1-Hydroxybenzotriazole → N-[[2-(3-chlorophenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[4-(1,1-dioxo-[1,2]thiazolidin-2-yl)-3-fluoro-phenyl]-propionamide

HRID 1842992Notes

Reaction equation

HRID 1842992 reaction equation
[O:1]=[S:2]1(=[O:19])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:17])[C:14]([OH:16])=O)=[CH:9][C:8]=1[F:18].ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[Cl:61][C:62]1[CH:63]=[C:64]([N:68]2[C:72]([CH2:73][NH2:74])=[CH:71][C:70]([C:75]([F:78])([F:77])[F:76])=[N:69]2)[CH:65]=[CH:66][CH:67]=1>C1COCC1>[Cl:61][C:62]1[CH:63]=[C:64]([N:68]2[C:72]([CH2:73][NH:74][C:14](=[O:16])[CH:13]([C:10]3[CH:11]=[CH:12][C:7]([N:3]4[CH2:4][CH2:5][CH2:6][S:2]4(=[O:1])=[O:19])=[C:8]([F:18])[CH:9]=3)[CH3:17])=[CH:71][C:70]([C:75]([F:76])([F:77])[F:78])=[N:69]2)[CH:65]=[CH:66][CH:67]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66644230(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamineHCID 708161742-[4-(1,1-Dioxo-[1,2]thiazolidin-2-yl)-3-fluoro-phenyl]-propionic acid

Product 1

HCID 70815734N-[[2-(3-chlorophenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[4-(1,1-dioxo-[1,2]thiazolidin-2-yl)-3-fluoro-phenyl]-propionamideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(1,1-Dioxo-[1,2]thiazolidin-2-yl)-3-fluoro-phenyl]-propionic acid (50 mg, 0.174 mmol) in THF (1.3 mL) was added 1-hydroxybenzotriazole (23 mg, 0.174 mmol), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumtetrafluoroborate (56 mg, 0.174 mmol), n-ethyldiisopropylamine (0.059 mL, 0.348 mmol) and (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine (47 mg, 0.174 mmol). The reaction mixture was stirred for 48 h at room temperature. The reaction mixture was concentrated in vacuo and purified by column chromatography (eluent: ethyl acetate/cyclohexan (2:1)) to give pure N-[[2-(3-chlorophenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[4-(1,1-dioxo-[1,2]thiazolidin-2-yl)-3-fluoro-phenyl]-propionamide (example compound C1) (68 mg, 72%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography (eluent: ethyl acetate/cyclohexan (2:1))

Sources & evidence

ORD record
ord-b0ea6c52274f4d65a953c6c7d296e72c
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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