Triethylamine → HCID 86650346, compound

HRID 1186695Notes

Reaction equation

HRID 1186695 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13](O)=[O:14])=[CH:11][N:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.NO.F[P-](F)(F)(F)(F)F.[N:34]1([O:43][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([NH:34][OH:43])=[O:14])=[CH:11][N:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 66864585HCID 66864585, compound

Product 1

HCID 86650346HCID 86650346, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(4-bromophenyl)-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid 65 (0.30 g, 0.804 mmol), hydroxylamine hydrochloride (0.112 g, 1.608 mmol), BOP (0.427 g, 0.965 mmol) and triethylamine (0.336 mLs, 2.412 mmol) in pyridine (10 mLs) was stirred at room temperature for 2 h. All solvents were then removed under reduced pressure, and the residue diluted with brine and aq. HCl until pH=1. Following extraction with EtOAc, the combined organic extracts were dried with anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel using 50-100% EtOAc/hexanes as the eluent to afford title compound 66 (10 mgs, 3% yield) as a light orange solid.

Workup

  1. customAll solvents were then removed under reduced pressure
  2. additionthe residue diluted with brine and aq. HCl until pH=1
  3. extractionextraction with EtOAc
  4. dry with materialthe combined organic extracts were dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel using 50-100% EtOAc/hexanes as the eluent

Sources & evidence

ORD record
ord-e41ef107e518441ca9304f2c7de3d8a1
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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