Water → HCID 25190385, compound

HRID 219764Notes

Reaction equation

HRID 219764 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](=[O:12])[C:5]2([NH:20][C:21](=[O:30])[CH2:22][N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.[H-].[Na+].[C:33]1([C:39](Cl)=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>CN(C=O)C>[C:39]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[C:10]([Cl:11])[CH:9]=2)[C:5]([NH:20][C:21](=[O:30])[CH2:22][N:23]2[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]2)([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:6]1=[O:12])(=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 25190330HCID 25190330, compound

Product 1

HCID 25190385HCID 25190385, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.14 g of the compound of Example 1 is placed in 9 ml of DMF in a round-bottomed flask equipped with a magnetic stirrer, and under a stream of nitrogen. 0.01 g of 60% NaH is added, at 0° C. PhCOCl is then added dropwise and the mixture is left to react at room temperature for 2 hours. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. 120 mg of oil are obtained, which product is purified on a column by flash chromatography, eluting with 95/5 ethyl acetate/methanol, to isolate 20 mg of white solid.

Workup

  1. customequipped with a magnetic stirrer
  2. waitthe mixture is left
  3. customto react at room temperature for 2 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-652293a88b6c454c945d06b9500bf934
Source dataset
uspto-grants-2012_06
Patent number
US08202871B2

Reaction notes

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