Ethanolamine → 5-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-N-(2-hydroxyethyl)-1-phenyl-1H-Pyrazole-3-carboxamide

HRID 522078Notes

Reaction equation

HRID 522078 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[C:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([OH:20])=O)[CH:8]=1)=[O:5].[CH2:33]([CH2:35][NH2:36])[OH:34].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C)C=O>[NH3:6].[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[C:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([NH:36][CH2:35][CH2:33][OH:34])=[O:20])[CH:8]=1)=[O:5]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1184970945-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid

Product 2

HCID 222AmmoniaHCID 1184971025-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-N-(2-hydroxyethyl)-1-phenyl-1H-Pyrazole-3-carboxamideYield 144.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 102, 100 mg, 0.212 mmol), ethanolamine (0.2 mL, 0.32 mmol) and HATU (121 mg, 0.32 mmol) were dissolved in dimethylformamide (5 mL) under nitrogen. Triethylamine (0.12 mL, 0.85 mmol) was added and the reaction stirred at room temperature for 1 hour. The reaction was concentrated in vacuo. The residue was partitioned between ethyl acetate (50 mL) and water (30 mL), the organic layer was collected, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 95:5:0.5 dichloromethane:methanol:ammonia to afford the title compound as a white solid (79 mg, 73%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate (50 mL) and water (30 mL)
  3. customthe organic layer was collected
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 95:5:0.5 dichloromethane

Sources & evidence

ORD record
ord-02ded676a6594f60b327dca1cbc56faa
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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