Methyl 4-aminobenzoate → HCID 23152494, compound

HRID 1012324Notes

Reaction equation

HRID 1012324 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][C:30]([CH3:35])([CH3:34])[C:31](O)=[O:32])=[O:28])=[CH:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[NH2:40][C:41]1[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1.CN(C)C=O>[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][C:30]([CH3:34])([CH3:35])[C:31]([NH:40][C:41]4[CH:42]=[CH:43][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:49][CH:50]=4)=[O:32])=[O:28])=[CH:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 12082Methyl 4-aminobenzoate2×HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 23152318HCID 23152318, compound

Product 1

HCID 23152494HCID 23152494, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolvent2×HCID 6212ChloroformSolvent3×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-2-methylpropionic acid (200 mg, 0.42 mmol) in chloroform (4.0 ml) was added a catalytic amount of N,N-dimethylformamide solution, thionyl chloride (0.07 ml, 1.26 mmol) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Then, and the solvent was evaporated under reduced pressure to give a yellow solid. The obtained solid was dissolved in chloroform (1.5 ml), and added dropwise to a solution of methyl 4-aminobenzoate (95.2 mg, 0.63 mmol) in a mixture of chloroform (1.0 ml) and pyridine (1.0 ml) under ice-cooling. Then, methyl 4-aminobenzoate (32 mg, 0.21 mmol) and pyridine (2.0 ml) were added, and the mixture was stirred at room temperature for 24 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. Methanol and chloroform were added to the residue, and the mixture was stirred. The precipitate was collected by filtration to give methyl 4-{2-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-2-methylpropionylamino}benzoate (105 mg, yield 41%).

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. customThen, and the solvent was evaporated under reduced pressure
  4. customto give a yellow solid
  5. temperaturecooling
  6. stirringthe mixture was stirred at room temperature for 24 hr
  7. extractionthe mixture was extracted with chloroform
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationAfter filtration
  11. customthe solvent was evaporated under reduced pressure
  12. additionMethanol and chloroform were added to the residue
  13. stirringthe mixture was stirred
  14. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-e5dd19bb6e1e480fbabf02913520141a
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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