Dimethylformamide → HCID 44588774, compound

HRID 2075592Notes

Reaction equation

HRID 2075592 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:17](=[O:21])[C:18]([OH:20])=O)[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[N:33]1([CH2:39][CH2:40][O:41][C:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]([NH2:52])=[CH:44][CH:43]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CCOC(C)=O.C([O-])(O)=O.[Na+]>[C:1]([C:5]1[CH:6]=[C:7]([C:17](=[O:21])[C:18]([NH:52][C:45]2[C:46]3[C:51](=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:42]([O:41][CH2:40][CH2:39][N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:43][CH:44]=2)=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 110439124-(2-Morpholinoethoxy)naphthalen-1-amineHCID 67091467HCID 67091467, compound

Product 1

HCID 44588774HCID 44588774, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To the crude (5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-oxo-acetic acid 34 (0.4 g, 1.4 mmol) in a 40 mL scintillation vial was added oxalyl Chloride (5 mL) and on drop of DMF. The suspension was stirred at rt for 1 h, and concentrated under vacuum. The resulting solid was dissolved in EtOAc (10 mL) and added to 4-(2-Morpholin-4-yl-ethoxy)-naphthalen-1-ylamine (0.45 g, 1.2 mmol) dissolved in EtOAc (10 mL)/50% NaHCO3 (10 mL) and stirred overnight at rt. The mixture was diluted with EtOAc and extracted with NaHCO3. The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent removed affording a dark brown oil. The material was purified by column chromatography (50-100% EtOAc/Hexanes) providing 0.357 g (57%) of the desired compound as a yellow solid. Expected mass=540. Observed mass=541.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe resulting solid was dissolved in EtOAc (10 mL)
  3. stirringstirred overnight at rt
  4. extractionextracted with NaHCO3
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. customaffording a dark brown oil
  10. customThe material was purified by column chromatography (50-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-417f8a41d35649668d7db16dbb40335e
Source dataset
uspto-grants-2011_04
Patent number
US07919617B2

Reaction notes

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