Diisopropylethylamine → 1-(4-Chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [1-(5-bromo-pyridin-3-yl)-butyl]-amide

HRID 2067965Notes

Reaction equation

HRID 2067965 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:12])[CH2:9][CH2:10][CH3:11])[CH:5]=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[C:33]([CH3:34])=[C:32]([C:35](Cl)=[O:36])[CH:31]=[N:30]2)=[CH:25][CH:24]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:12][C:35]([C:32]2[CH:31]=[N:30][N:29]([C:26]3[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=3)[C:33]=2[CH3:34])=[O:36])[CH2:9][CH2:10][CH3:11])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27761281-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carbonyl chlorideHCID 584433761-(5-Bromo-pyridin-3-yl)-butylamine

Product 1

HCID 444805971-(4-Chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [1-(5-bromo-pyridin-3-yl)-butyl]-amideYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(5-bromo-pyridin-3-yl)-butylamine (470 mg, 2.0 mmol), diisopropylethylamine (0.82 mL, 4.7 mmol) and DMAP (19 mg, 0.16 mmol) in CH2Cl2 (20 mL) is treated with 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carbonyl chloride (400 mg, 1.6 mmol) and stirred for 15 hours. The reaction mixture is then diluted with CH2Cl2 (50 mL), washed with saturated aqueous ammonium chloride (2×50 mL) and brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material is purified by flash chromatography on silica gel (eluted with 20 to 50% EtOAc/hexanes) to provide 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [1-(5-bromo-pyridin-3-yl)-butyl]amide as a colorless foam-solid (540 mg, 78%).

Workup

  1. washwashed with saturated aqueous ammonium chloride (2×50 mL) and brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material is purified by flash chromatography on silica gel (eluted with 20 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6e3d97bd0b8a4995bf7457b35a958111
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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