HCID 68921193, compound → HCID 11634289, compound

HRID 1785941Notes

Reaction equation

HRID 1785941 reaction equation
C(OC([N:6]1[C:11]2[CH:12]=[C:13]([C:16]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]([N:28]([C:36](=[O:38])[CH3:37])[C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[CH2:20][CH:19]3[CH3:39])=[O:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1)=O)C>C(Cl)Cl.I[Si](C)(C)C>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([N:28]([C@H:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:18]([C:16]([C:13]3[CH:14]=[CH:15][C:10]4[O:9][CH2:8][CH2:7][NH:6][C:11]=4[CH:12]=3)=[O:17])[C@@H:19]([CH3:39])[CH2:20]2)[C:36](=[O:38])[CH3:37])=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 68921193HCID 68921193, compound

Product 1

HCID 11634289HCID 11634289, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 85247Trimethylsilyl iodideSolvent

Procedure

6-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid ethyl ester was dissolved in methylene chloride (3 mL) and iodotrimethylsilane (1 mL). After 4 days, the reaction was quenched with sat. aq. NaHCO3. The residue was partitioned between methylene chloride and water, then extracted three times with methylene chloride, dried over MgSO4, filtered and concentrated. The crude residue was purified by silica gel chromatography (ethyl acetate) to afford the product.

Workup

  1. customthe reaction was quenched with sat. aq. NaHCO3
  2. customThe residue was partitioned between methylene chloride and water
  3. extractionextracted three times with methylene chloride
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel chromatography (ethyl acetate)
  8. customto afford the product

Sources & evidence

ORD record
ord-fe3797a7dbed47b6b5a5670b3a947a45
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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