Water → HCID 41121420, compound

HRID 1785869Notes

Reaction equation

HRID 1785869 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][C@@H:9]1[CH3:25])=[O:7].C(N(C(C)C)CC)(C)C.[C:35](Cl)(=[O:37])[CH3:36].O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11]([N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:35](=[O:37])[CH3:36])[CH2:10][C@@H:9]1[CH3:25])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 667751HCID 667751, compound

Product 1

HCID 41121420HCID 41121420, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-cis-furan-2-yl-(2-methyl-4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-methanone (360 mg, 1.0 mmol) in methylene chloride (5 mL) was added diisopropylethylamine (1.9 mL, 10 mmol) followed by acetyl chloride (388 uL, 5 mmol). The mixture was stirred at room temperature over night. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with 1 M (aq) NaOH and brine, dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (50% hexanes/50% ethyl acetate) to afford the amide (230 mg, 57%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with 1 M (aq) NaOH and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography (50% hexanes/50% ethyl acetate)

Sources & evidence

ORD record
ord-1fb80b431d5b444e92a070f5b8a78d59
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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