N-Methylacetamide → HCID 71294469, compound

HRID 1747560Notes

Reaction equation

HRID 1747560 reaction equation
[CH3:1][NH:2][C:3](=[O:5])[CH3:4].N1C(C)=CC=CC=1C.C(Cl)(=O)C(Cl)=O.[F:20][C:21]([F:57])([F:56])[CH:22]([C:49]1[CH:54]=[CH:53][N+:52]([O-])=[CH:51][CH:50]=1)[O:23][C:24]1[C:33]([N:34]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[S:35]([CH2:38][CH2:39][CH3:40])(=[O:37])=[O:36])=[N:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1.C(=O)(O)[O-].[Na+]>ClCCl.O>[CH3:1][N:2]([C:53]1[CH:54]=[C:49]([CH:22]([O:23][C:24]2[C:33]([N:34]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:47])([CH3:46])[CH3:48])[S:35]([CH2:38][CH2:39][CH3:40])(=[O:37])=[O:36])=[N:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)[C:21]([F:20])([F:57])[F:56])[CH:50]=[CH:51][N:52]=1)[C:3](=[O:5])[CH3:4]

Participants

8

Reactant 5

HCID 6582N-MethylacetamideHCID 79372,6-LutidineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 86678206HCID 86678206, compound

Product 1

HCID 71294469HCID 71294469, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-methylacetamide (0.097 mL, 1.30 mmol) was dissolved in dichloromethane (1.0 mL). To the solution were added at 0° C. 2,6-lutidine (0.30 mL, 2.5 mmol) and oxalyl dichloride (0.11 mL, 1.30 mmol). After stirring at the same temperature for 15 minutes, a solution of Compound B4 (145 mg, 0.253 mmol) obtained in Step 1 of Example 42 in dichloromethane (1.0 mL) was added and the mixture was further stirred at room temperature for 18 hours. A saturated aqueous sodium bicarbonate solution and water were added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=1/10) to give Compound B7 (157 mg, 99% yield).

Workup

  1. additionTo the solution were added at 0° C
  2. stirringthe mixture was further stirred at room temperature for 18 hours
  3. extractionExtraction with ethyl acetate
  4. dry with materialdrying over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=1/10)

Sources & evidence

ORD record
ord-7eea97ee6b0b47cea3e22d1b3c6fa20e
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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