Pyridine → HCID 71283441, compound

HRID 335315Notes

Reaction equation

HRID 335315 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([N:13]=[CH:14][C:15]=3[C:16]([OH:18])=O)[CH:12]=2)=[CH:5][CH:4]=[N:3]1.[N:19]1C=CC=CC=1.[CH3:25][C:26]1[CH:34]=[CH:33]C(C([O-])=O)=[CH:28][N:27]=1.C[CH2:36][O:37][C:38]([CH3:40])=[O:39]>>[CH3:25][C:26]1[C:34]([NH:19][C:16]([C:15]2[CH:14]=[N:13][N:11]3[CH:12]=[C:7]([C:6]4[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=4)[CH:8]=[CH:9][C:10]=23)=[O:18])=[CH:33][C:40]([C:38]([O:37][CH3:36])=[O:39])=[CH:28][N:27]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 6950482HCID 6950482, compoundHCID 71283429HCID 71283429, compound

Product 1

HCID 71283441HCID 71283441, compound

Procedure

6-(1-Methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (step 2) was dissolved in pyridine (5 ml, 61.8 mmol) and 6-methylnicotinate (247 mg, 1.486 mmol) was added. The reaction mixture was stirred under nitrogen overnight. The mixture was diluted with EtOAc (200 ml) and washed with sat. aq. NaHCO3 (200 ml). The aqueous portion was back-extracted with EtOAc (100 ml) and the combined organic extracts were, dried MgSO4, filtered and concentrated under vacuum to give yellow solid. Purification of the solid by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/TBME afforded the title compound;

Workup

  1. washwashed with sat. aq. NaHCO3 (200 ml)
  2. extractionThe aqueous portion was back-extracted with EtOAc (100 ml)
  3. filtrationdried MgSO4, filtered
  4. concentrationconcentrated under vacuum
  5. customto give yellow solid
  6. customPurification of the solid by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/TBME

Sources & evidence

ORD record
ord-eb2d8784dde940318272567248c0da66
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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