Pyrrolidine → HCID 18769383, compound

HRID 480398Notes

Reaction equation

HRID 480398 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:20]=[C:13]3[N:14]=[C:15]([CH3:19])[CH:16]=[C:17](Cl)[N:12]3[N:11]=2)=[CH:6][CH:5]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CN1CCCC1=O>[CH3:19][C:15]1[CH:16]=[C:17]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[N:12]2[N:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:21])=[CH:5][CH:6]=3)[CH:20]=[C:13]2[N:14]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86585217HCID 86585217, compound

Product 1

HCID 18769383HCID 18769383, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(7-chloro-5-methyl-pyrazolo[1,5-a]pyrimidin-2-yl)-benzoic acid methyl ester (15.1 mmol) in 1-methyl-2-pyrrolidinone (50 ml) was added pyrrolidine (151 mmol) and the reaction heated at 80° C. for 72 hours. The resultant solid precipitate was filtered and dried under vacuum, then dissolved in 10% NaOH and the aqueous phase washed with ethyl acetate, acidified with conc. HCl, and the resultant precipitated white solid filtered and dried under vacuum to afford 4-(5-Methyl-7-pyrrolidin-1-yl-pyrazolo[1,5-a]pyrimidin-2-yl)-benzoic acid. (3.9 g, 80% yield) MS m/z @323 (m+1).

Workup

  1. filtrationThe resultant solid precipitate was filtered
  2. customdried under vacuum
  3. dissolutiondissolved in 10% NaOH
  4. washthe aqueous phase washed with ethyl acetate
  5. customthe resultant precipitated white solid
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-7d346329953b42cfb83fa2d642e955d1
Source dataset
uspto-grants-2003_11
Patent number
US06649759B2

Reaction notes

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