Pyridine → Methyl 6-methyl-5-(6-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridine-3-carboxamido)nicotinate

HRID 335315노트

반응식

HRID 335315 반응식
[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

참가 물질

5

반응물 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 6950482HCID 6950482, 화합물HCID 71283429HCID 71283429, 화합물

생성물 1

HCID 71283441Methyl 6-methyl-5-(6-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridine-3-carboxamido)nicotinate

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-eb2d8784dde940318272567248c0da66
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883819B2

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