HCID 719836, compound → HCID 58958171, compound

HRID 914988Notes

Reaction equation

HRID 914988 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][C:12]([NH:14][NH2:15])=[O:13].C[Al](C)C.[CH3:20][C:21]1[CH:30]=[C:29]([NH:31][C:32]2[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=2)[C:35](OC)=[O:36])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1>C1(C)C(C)=CC=CC=1>[CH3:20][C:21]1[CH:30]=[C:29]([NH:31][C:32]2[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=2)[C:35]([NH:15][NH:14][C:12](=[O:13])[CH2:11][N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[O:36])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1

Participants

5

Reactant 3

HCID 719836HCID 719836, compoundHCID 16682925TrimethylaluminumHCID 27055575HCID 27055575, compound

Product 1

HCID 58958171HCID 58958171, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 91 (205 mg, 1.0 mmol) in xylene (5 mL) was added trimethyl aluminum (2 M solution in hexanes, 0.75 mL, 1.5 mmol). The mixture was stirred under nitrogen for 10 minutes before the addition of methyl 3-(2-methylquinolin-4-ylamino)benzoate (49) (150 mg, 0.5 mmol). The reaction was heated at reflux overnight, quenched with water (2 mL), basified to pH 9 (2 N NaOH), and extracted with 7:3 CH2Cl2/MeOH. The organic layer was dried (K2CO3) and concentrated under reduced pressure, and the residue was purified by flash chromatography (SiO2, gradient elution) to give 92 as a pale yellow oil (147 mg, 63%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. customquenched with water (2 mL)
  4. extractionextracted with 7:3 CH2Cl2/MeOH
  5. dry with materialThe organic layer was dried (K2CO3)
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by flash chromatography (SiO2, gradient elution)

Sources & evidence

ORD record
ord-1bdbe100c69249d79026c9f119f6012f
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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