Water → HCID 22267231, compound

HRID 488870Notes

Reaction equation

HRID 488870 reaction equation
CNCC1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:14])[O:10][C:9](=[O:15])[C:8]([CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[C:27]([F:30])([F:29])[F:28])=[O:18])=[C:7]2[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[CH2:37]([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])C.C(Cl)(=[O:46])C.O>C1COCC1>[C:40]([N:39]([CH2:42][C:43]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:14])[O:10][C:9](=[O:15])[C:8]([CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[C:27]([F:29])([F:30])[F:28])=[O:18])=[C:7]2[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH3:37])(=[O:46])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22267270HCID 22267270, compound

Product 1

HCID 22267231HCID 22267231, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[6-[(methylamino)methyl]-7-chloro-2-oxo-4-phenyl-2H-chromen-3-yl]-N-[4-chloro-2-(trifluoromethyl)phenyl]acetamide (Example 180)(0.20 g) in THF (5 ml) was combined with triethylamine (0.11 ml) and acetyl chloride (0.033 ml), and stirred for 3 hours. The reaction solution was combined with water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate followed by a saturated brine, and then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant residue was purified by column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:4), and further recrystallized from ethyl acetate-diisopropyl ether to obtain the title compound as a colorless crystal (105 mg, 48%). Melting point: 199-201° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant residue was purified by column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:4)
  6. customfurther recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-7c4b1c9c77434934b3eea2f6ea3d70c2
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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