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 1157774ノート

反応式

HRID 1157774 の反応式
[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

参加物

4

反応物 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

生成物 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-carbaldehyde収率 36.5%

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1d15429354b8456fb70b35de90fc73d6
出典データセット
uspto-grants-2010_10
特許番号
US07807676B2

反応ノート

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