Water → HCID 19386883, compound

HRID 1655386Notes

Reaction equation

HRID 1655386 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH2:14][NH2:15])=[C:8]([N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])[C:7]=2[CH:23]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].O>ClCCl>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[C:9]([CH2:14][NH:15][C:33](=[O:35])[CH3:34])=[C:8]([N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])[C:7]=2[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19387040HCID 19387040, compound

Product 1

HCID 19386883HCID 19386883, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 6-trifluoromethyl-2,2-dimethyl-3-aminomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.68 g, 1.82 mmol) and triethylamine (0.3 ml, 2.18 mmol) in dichloromethane (18 ml), acetyl chloride (0.15 ml, 2.18 mmol) was added at room temperature. The solution was stirred for 6 hours and then water added. The organic layer was separated, dried and evaporated, to give crude product which was chromatographed on silica gel. Elution with dichloromethane/methanol (95/5) gave a product which was crystallized from ether to afford 0.3 g of 6-trifluoromethyl-2,2-dimethyl-3-(acetamido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)2H-1-benzopyran, m.p. 174° C.

Workup

  1. additionwas added at room temperature
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated
  5. customto give crude product which
  6. customwas chromatographed on silica gel
  7. washElution with dichloromethane/methanol (95/5)
  8. customgave a product which
  9. customwas crystallized from ether

Sources & evidence

ORD record
ord-0782bde5231a48db8e0daf613608c09c
Source dataset
uspto-grants-1993_10
Patent number
US05250547

Reaction notes

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