Diisopropylethylamine → 5-Methyl-2-(2H-1,2,3-triazol-2-yl)-N-(2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)benzamide

HRID 1750593Notes

Reaction equation

HRID 1750593 reaction equation
Cl.[F:2][C:3]([F:18])([F:17])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[NH2:16])=[N:8][CH:9]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:50][C:51]1[CH:52]=[CH:53][C:54]([N:60]2[N:64]=[CH:63][CH:62]=[N:61]2)=[C:55]([CH:59]=1)[C:56](O)=[O:57]>CN(C=O)C>[CH3:50][C:51]1[CH:52]=[CH:53][C:54]([N:60]2[N:64]=[CH:63][CH:62]=[N:61]2)=[C:55]([CH:59]=1)[C:56]([NH:16][CH:12]1[CH2:13][CH2:14][CH2:15][CH:11]1[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([F:17])([F:2])[F:18])=[CH:9][N:8]=1)=[O:57]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 1183082132-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine hydrochloride2×

Product 1

HCID 1183081055-Methyl-2-(2H-1,2,3-triazol-2-yl)-N-(2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine hydrochloride (Intermediate 36; 0.60 g, 2.44 mmol) in DMF (5 ml) was added DIPEA (0.63 g, 4.80 mmol), TBTU (0.94 g, 2.93 mmol) and added 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 6; 0.49 g, 2.44 mmol). The reaction was stirred at room temperature for 1 hour and then partitioned between ethyl acetate (50 ml) and water (10.0 ml). The aqueous layer was further extracted with ethyl acetate (50 ml) and the combined organics were concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-2% methanol/DCM) to afford the title compound.

Workup

  1. custompartitioned between ethyl acetate (50 ml) and water (10.0 ml)
  2. extractionThe aqueous layer was further extracted with ethyl acetate (50 ml)
  3. concentrationthe combined organics were concentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (silica, 0-2% methanol/DCM)

Sources & evidence

ORD record
ord-1c7097eebfde4f138b56b5ec7dee5be8
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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