Dimethylformamide → HCID 74057845, compound

HRID 1884236Notes

Reaction equation

HRID 1884236 reaction equation
[F:1][CH:2]([F:27])[O:3][CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)=[O:7].CN(C)C=O.Cl[CH2:34][C:35]#[CH:36].[H-].[Na+]>O>[F:27][CH:2]([F:1])[O:3][CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:36][C:35]#[CH:34])=[C:13]([O:18][CH3:19])[CH:12]=1)=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 122213-Chloro-1-propyneHCID 24758Sodium hydrideHCID 69899072HCID 69899072, compound

Product 1

HCID 74057845HCID 74057845, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

477 mg (1.20 mmol) of 3-difluoromethoxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(4-chlorophenyl)acrylamide, 5 ml of anhydrous N,N-dimethylformamide, 180 mg (2.40 mmol) of 3-chloropropyne and 72 mg (1.80 mmol) of 60% sodium hydride were stirred at room temperature for 2 hours. Water was added to to the reaction mixture, which was followed by extracted with ethyl acetate, washed with 5% hydrochrolic acid, saturated aqueous sodium bicarbonate solution and saturated brine subsequently, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 70 mg of 3-difluoromethoxy-N-[2-{3-methoxy-4-(2-propynyloxy)phenyl}ethyl]-2-(4-chlorophenyl)acrylamide (the present compound 1355).

Workup

  1. extractionby extracted with ethyl acetate
  2. washwashed with 5% hydrochrolic acid, saturated aqueous sodium bicarbonate solution and saturated brine subsequently
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7bdf88f517ef485a8d10fbfecf909ec6
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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