Acetyl chloride → HCID 11691667, compound

HRID 1785944Notes

Reaction equation

HRID 1785944 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]([C:21]3[CH:31]=[CH:30][C:24]4[N:25]([CH3:29])[CH2:26][CH2:27][O:28][C:23]=4[CH:22]=3)=[O:20])[C@@H:11]([CH3:32])[CH2:10]2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:42](Cl)(=[O:44])[CH3:43]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]([C:21]3[CH:31]=[CH:30][C:24]4[N:25]([CH3:29])[CH2:26][CH2:27][O:28][C:23]=4[CH:22]=3)=[O:20])[C@@H:11]([CH3:32])[CH2:10]2)[C:42](=[O:44])[CH3:43])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68926340HCID 68926340, compound

Product 1

HCID 11691667HCID 11691667, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-[4-(4-Chloro-phenylamino)-2-methyl-3,4-dihydro-2H-quinolin-1-yl]-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-methanone (540 mg, 1.25 mmol) in methylene chloride (5 mL) was added diisopropylethylamine (0.240 mL, 1.37 mmol) followed by acetyl chloride (2 mL). The mixture was stirred at room temperature 4 hours. The mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with sat. aq. NaHCO3, brine and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (25/75 hexanes/ethyl acetate gradient) to afford the final product.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with sat. aq. NaHCO3, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (25/75 hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-1a88f1be5bad4005a59d44751fa43e7f
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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