Dimethylformamide → HCID 74057840, compound

HRID 1884234Notes

Reaction equation

HRID 1884234 reaction equation
[F:1][CH:2]([F:30])[O:3][CH:4]=[C:5]([C:20]1[CH:29]=[CH:28][C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[CH:21]=1)[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([OH:19])[CH:12]=1)=[O:7].CN(C)C=O.Cl[CH2:37][C:38]#[CH:39].[H-].[Na+]>O>[F:1][CH:2]([F:30])[O:3][CH:4]=[C:5]([C:20]1[CH:29]=[CH:28][C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[CH:21]=1)[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:39][C:38]#[CH:37])[CH:12]=1)=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 122213-Chloro-1-propyneHCID 24758Sodium hydrideHCID 69902780HCID 69902780, compound

Product 1

HCID 74057840HCID 74057840, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

417 mg (1.00 mmol) of 3-difluoromethoxy-N-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide, 5 ml of anhydrous N,N-dimethylformamide, 74 mg (1.00 mmol) of 3-chloropropyne and 50 mg (1.25 mmol) of 60% sodium hydride were mixed and stirred at room temperature for 3 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 to give 162 mg of 3-difluoromethoxy-N-[2-{4-methoxy-3-(2-propynyloxy)phenyl}ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide (the present compound 1299).

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-169baedae733499fb67299ed769b3236
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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