Ethyl 3-aminobenzoate → HCID 57635949, compound

HRID 2109979Notes

Reaction equation

HRID 2109979 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[CH:10][C:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17])=[C:4]2[N:3]=1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(O)C>[CH2:25]([O:24][C:22](=[O:23])[C:21]1[CH:27]=[CH:28][CH:29]=[C:19]([NH:18][C:6]2[N:5]3[N:9]=[CH:10][C:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17])=[C:4]3[N:3]=[C:2]([Cl:1])[CH:7]=2)[CH:20]=1)[CH3:26]

Participants

4

Reactant 2

HCID 11400Ethyl 3-aminobenzoateHCID 57635946HCID 57635946, compound

Product 1

HCID 57635949HCID 57635949, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of compound (13a) (1.24 g, 4.62 mmol) in 10 mL of ethanol was added ethyl 3-aminobenzoate (764 mg. 4.62 mmol). The reaction mixture was heated at 50° C. for 2 h and then cooled to room temperature. Solvent was removed and the residue was dissolved in EtOAc (50 mL) and washed with saturated aq NaHCO3, 10% HCl, and brine and dried over anhydrous Na2 SO4. Removal of the solvent provided a residue that was purified by flash column with use of EtOAc/hexane (25% to 50%) to yield 3-[5-chloro-3-(4-cyano-butyl)-pyrazolo[1,5-a]pyrimidin-7-ylamino]-benzoic acid ethyl ester (14a) (1.0 g. 50%).

Workup

  1. temperaturecooled to room temperature
  2. customSolvent was removed
  3. dissolutionthe residue was dissolved in EtOAc (50 mL)
  4. washwashed with saturated aq NaHCO3, 10% HCl, and brine
  5. customdried over anhydrous Na2 SO4
  6. customRemoval of the solvent
  7. customprovided a residue that
  8. customwas purified by flash column with use of EtOAc/hexane (25% to 50%)

Sources & evidence

ORD record
ord-538e2b698b33497186b93128b1c89206
Source dataset
uspto-grants-2009_04
Patent number
US07517882B2

Reaction notes

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