Water → 4-(4-methoxy-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazole-2-carbaldehyde

HRID 1157774노트

반응식

HRID 1157774 반응식
[O:1]1CCO[CH:2]1[C:6]1[S:7][CH:8]=[C:9]([C:11]2[N:12]=[CH:13][C:14]([O:41][CH3:42])=[C:15]3[C:19]([C:20](=[O:40])[C:21]([N:23]4[CH2:28][CH2:27][N:26]([C:29]5[N:33]([C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=6)[N:32]=[N:31][N:30]=5)[CH2:25][CH2:24]4)=[O:22])=[CH:18][NH:17][C:16]=23)[N:10]=1.O.C(O)(C(F)(F)F)=O>>[CH3:42][O:41][C:14]1[CH:13]=[N:12][C:11]([C:9]2[N:10]=[C:6]([CH:2]=[O:1])[S:7][CH:8]=2)=[C:16]2[NH:17][CH:18]=[C:19]([C:20](=[O:40])[C:21](=[O:22])[N:23]3[CH2:24][CH2:25][N:26]([C:29]4[N:33]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[N:32]=[N:31][N:30]=4)[CH2:27][CH2:28]3)[C:15]=12

참가 물질

4

반응물 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 497701741-[7-[2-(1,3-dioxolan-2-yl)thiazol-4-yl]-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]ethane-1,2-dione

생성물 1

HCID 595113084-(4-methoxy-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazole-2-carbaldehyde수율 36.5%

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온도
70 °C

실험 절차

To a suspension of 1-(7-(2-(1,3-dioxolan-2-yl)thiazol-4-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (0.305 g, 0.519 mmol) in H2O (2 mL, 111 mmol) was added TFA (1 mL, 12.98 mmol). The mixture was heated to 70° C. After 18 h of heating, the mixture was cooled to rt, and was stirred at rt for an additional 20 h. The mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and was partitioned with sat. NaHCO3. The mixture was extracted with dichloromethane (3×10 mL) and was dried with Na2SO4. The drying agent was removed by filtration. The organic solution was concentrated under reduced pressure, and the resulting mixture was purified by flash chromatography (0 to 5% methanol in dichloromethane gradient). The product, 4-(4-methoxy-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazole-2-carbaldehyde (0.103 g, 0.189 mmol, 36.5% yield) was collected as a light-yellow solid.

후처리

  1. temperatureAfter 18 h of heating
  2. temperaturethe mixture was cooled to rt
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. customwas partitioned with sat. NaHCO3
  6. extractionThe mixture was extracted with dichloromethane (3×10 mL)
  7. dry with materialwas dried with Na2SO4
  8. customThe drying agent was removed by filtration
  9. concentrationThe organic solution was concentrated under reduced pressure
  10. customthe resulting mixture was purified by flash chromatography (0 to 5% methanol in dichloromethane gradient)

출처 및 근거

ORD 기록
ord-1d15429354b8456fb70b35de90fc73d6
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807676B2

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