Pyridine → HCID 44210388, compound

HRID 1655522Notes

Reaction equation

HRID 1655522 reaction equation
[CH:1]1([C:4]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[NH:30][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])=[CH:20][CH:19]=3)=[C:7]3[N:8]=[C:9]([C:13]([OH:15])=[O:14])[CH:10]=[C:11]([CH3:12])[N:6]3[N:5]=2)[CH2:3][CH2:2]1.N1C=CC=C[CH:39]=1>CO>[CH:1]1([C:4]2[C:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[NH:30][S:31]([C:34]([F:36])([F:35])[F:37])(=[O:33])=[O:32])=[CH:22][CH:23]=3)=[C:7]3[N:8]=[C:9]([C:13]([O:15][CH3:39])=[O:14])[CH:10]=[C:11]([CH3:12])[N:6]3[N:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 1049PyridineHCID 44210387HCID 44210387, compound

Product 1

HCID 44210388HCID 44210388, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 273 mg 2-cyclopropyl-7-methyl-3-[(-2'-(((trifluoromethyl)sulfonyl)amino)biphen-4-yl)methyl]pyrazolo[1,5-a]pyrimidine-5-carboxylic acid in 150 mL methanol was added 5 g Amberlyst-15. The mixture was heated to 60° C. for 9 hours (overnight generally preferred). After cooling to room temperature, 5 mL pyridine was added and the mixture was stirred for 30 minutes. The mixture was filtered, was stripped of solvent in vacuo, was stripped from toluene, then was chromatographed on silica gel under medium pressure using 1/1/98 HOAc/MeOH/CH2Cl2 to give 91 mg of the title compound (32% yield) as a yellow solid. Rf 0.58 in 1/3/96 HOAc/MeOH/CH2Cl2, visualized by white light, UV, iodine, and ammonium molybdate/ceric sulfate stain.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe mixture was filtered
  3. customwas chromatographed on silica gel under medium pressure

Sources & evidence

ORD record
ord-56bd38b3816e472eb1a976915be5d4c3
Source dataset
uspto-grants-1993_10
Patent number
US05250521

Reaction notes

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