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Dimethylformamide → N-Hydroxy-3-[1-(4-methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-N-methylpropanamide Monoformate

HRID 5016
Notes
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Reaction equation

HRID 5016 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[CH:13][C:12]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[N:11]2)=[CH:6][CH:5]=1.[CH3:26][N:27]([CH:29]=[O:30])C.C(Cl)(=O)C(Cl)=[O:33]>C(Cl)Cl>[CH:23]([OH:25])=[O:24].[OH:33][N:27]([CH3:26])[C:29](=[O:30])[CH2:22][CH2:21][C:12]1[CH:13]=[C:14]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=2)[N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 678573363-[1-(4-Methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-propionic acid hydrochloride

Product 1

HCID 19797563N-Hydroxy-3-[1-(4-methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-N-methylpropanamide Monoformate

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a solution of compound 31 (0.9 g, 2 5 mM) in CH2Cl2 (25 ml) at RT was added DMF (0.2 ml) and oxalyl chloride (1.26 g, 10 mM). After stirring for 0.5 hr, the reaction mixture was evaporated in vacuo, redissolved in CH2Cl2 (25 ml) and added dropwise to a solution of methylhydroxylamine hydrochloride (0.84 g, 10 mM) and Et3N (3.7 ml) in CH2Cl2 (50 ml) at 0° C. The reaction was stirred for 10 min and poured into a 1:1 stirred mixture of Ch2Cl2 :H2O. The CH2Cl2 layer was separated, washed (H2O and then brine), dried (Na2SO4) and evaporated in vacuo to give a semi-solid which was purified by column chromatography on Silica employing Hexane:40EtOAc:1% MeOH:0.1% HCO2H as eluent. The title compound 35 was obtained as a tan foam as the monoformate salt; MS, m/e 352 (M+).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionredissolved in CH2Cl2 (25 ml)
  3. additionadded dropwise to a solution of methylhydroxylamine hydrochloride (0.84 g, 10 mM) and Et3N (3.7 ml) in CH2Cl2 (50 ml) at 0° C
  4. stirringThe reaction was stirred for 10 min
  5. additionpoured into a 1:1
  6. stirringstirred
  7. additionmixture of Ch2Cl2
  8. customThe CH2Cl2 layer was separated
  9. washwashed (H2O
  10. dry with materialbrine), dried (Na2SO4)
  11. customevaporated in vacuo
  12. customto give a semi-solid which
  13. customwas purified by column chromatography on Silica

Sources & evidence

ORD record
ord-8a523d4abd2d452793523bb1a14f206d
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05242940

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes