Citric Acid → HCID 71178944, compound

HRID 2409269Notes

Reaction equation

HRID 2409269 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[N:32]3[N:33]=[CH:34][C:35]([S:36]([NH2:39])(=[O:38])=[O:37])=[C:31]3[N:30]=[CH:29][C:28]=2[C:40]([N:42]2[CH2:47][CH2:46][CH:45]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:44][CH2:43]2)=[O:41])=[C:22]([CH3:54])[CH:21]=1.N12CCCN=C1CCCCC2.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[N:32]3[N:33]=[CH:34][C:35]([S:36]([NH:39][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:6])(=[O:38])=[O:37])=[C:31]3[N:30]=[CH:29][C:28]=2[C:40]([N:42]2[CH2:47][CH2:46][CH:45]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:44][CH2:43]2)=[O:41])=[C:22]([CH3:54])[CH:21]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 15655Cyclopropanecarboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 71178940HCID 71178940, compound

Product 1

HCID 71178944HCID 71178944, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopropanecarboxylic acid (0.066 g, 0.768 mmol) was dissolved in DMF (0.8 mL), and 1,1′-carbonyldiimidazole (0.125 g, 0.768 mmol) was added. After stirring at room temperature for 30 min, 7-(4-fluoro-2-methylphenylamino)-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-sulfonamide (0.078 g, 0.154 mmol) obtained in step 5 and 1,8-diazabicyclo[5.4.0]undeca-7-en (0.140 g, 0.922 mmol) were added, and the mixture was stirred at 80° C. for 3 hr. 5% Aqueous citric acid solution was added to quench the reaction, and the precipitated crystals were collected by filtration. The obtained crystals were purified by silica gel column chromatography (chloroform/methanol=10/1) to give the title compound (0.026 g, 29%).

Workup

  1. stirringthe mixture was stirred at 80° C. for 3 hr
  2. customto quench
  3. customthe reaction
  4. filtrationthe precipitated crystals were collected by filtration
  5. customThe obtained crystals were purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-9d540d5826a5499dbb444eec06cdb061
Source dataset
uspto-grants-2014_08
Patent number
US08815874B2

Reaction notes

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