HCID 68921019, compound → HCID 57595539, compound

HRID 1786018Notes

Reaction equation

HRID 1786018 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:35])[C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][C:32](=[O:34])[CH3:33])=[CH:25][CH:24]=3)[C@@H:14]([CH3:36])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH3:37][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:35])[C:23]3[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][CH2:31][C:32]([OH:34])([CH3:37])[CH3:33])=[CH:27][CH:28]=3)[C@@H:14]([CH3:36])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68921019HCID 68921019, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 57595539HCID 57595539, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1-(4-(4-oxopentyl)benzoyl)-1,2,3,4-tetrahydroquinolin-4-yl)acetamide (40 mg, 0.079 mmol) in THF (2 mL), was added MeMgBr (68 uL, 0.095 mmol, 1.4 M solution in THF) at 0° C. The mixture was stirred at 0° C. for 2 h. After quenching with sat. NH4Cl solution, the mixture was extracted with EtOAc. The combined organic phases were dried over MgSO4 and concentrated. The residue was purified by column chromatography (EtOAc) to give 16 mg of desired product as a white solid (40% yield).

Workup

  1. customAfter quenching with sat. NH4Cl solution
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-12ca8a4bd50c4230a6f0da0d9d204f48
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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