p-Toluenesulfonic acid → HCID 178518488, compound

HRID 624709Notes

Reaction equation

HRID 624709 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[C:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[C:4]2[N:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN1C(=O)CCC1>[Cl:23][C:24]1[CH:25]=[C:26]([NH:27][C:2]2[CH:7]=[C:6]([NH:8][CH:9]3[CH2:11][CH2:10]3)[N:5]3[N:12]=[CH:13][C:14]([CH:15]=[C:16]4[S:20][C:19](=[O:21])[NH:18][C:17]4=[O:22])=[C:4]3[N:3]=2)[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 79323-ChloroanilineHCID 178518479HCID 178518479, compound

Product 1

HCID 178518488HCID 178518488, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

To 5-((5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione (20 mg, 0.06 mmol) in NMP was added 3-chloroaniline (38 μL, 0.36 mmol) and a few granules of p-toluenesulfonic acid. The reaction was heated in microwave at 180° C. 1.5 hours. The reaction mixture was filtered and purified by prep HPLC then prep TLC (1% MeOH/DCM) to yield 5-((5-(3-chlorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione as a yellow solid. LCMS (M+1=427)

Workup

  1. custom1.5 hours
  2. filtrationThe reaction mixture was filtered
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-f5b59c05b90b40da91a45b3c8d5c8a73
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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