Sulfamic Acid → 2-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

HRID 1898492노트

반응식

HRID 1898492 반응식
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]3[C:16]([CH:17]=[O:18])=[CH:15][N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:11]3=[N:12][CH:13]=2)[CH:5]=[N:4]1)[CH3:2].S(=O)(=O)([OH:29])N.[O-]Cl=O.[Na+].OP([O-])(O)=O.[K+]>O1CCOCC1.O>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]3[C:16]([C:17]([OH:29])=[O:18])=[CH:15][N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:25])([CH3:24])[CH3:26])[C:11]3=[N:12][CH:13]=2)[CH:5]=[N:4]1)[CH3:2]

참가 물질

7

반응물 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 866578682-(1-Ethyl-1H-pyrazol-4-yl)-5-[[2-(trimethylsilyl)ethoxy]methyl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxaldehyde

생성물 1

HCID 584385442-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid수율 90%

시약·촉매·용매 2

HCID 962Water용매3회HCID 312751,4-Dioxane용매

실험 절차

To a solution of 2-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (1.12 g, 3.01 mmol) in 1,4-dioxane (50 mL) and H2O (10 mL) at 0° C. was added sulfamic acid (1.76 g, 18.1 mmol). Then added a solution of NaClO2 (0.44 g, 3.92 mmol) and KH2PO4 (4.92 g, 36.2 mmol) in H2O (30 mL) via dropping funnel over 15 min. The ice bath was removed and the yellow cloudy reaction mixture was stirred at room temperature for 2.5 h. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4 and concentrated to an oily yellow solid which was triturated with 5% EtOAc/hexanes to afford 1.05 g (90%) of 2-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid as a light yellow solid.

후처리

  1. customover 15 min
  2. customThe ice bath was removed
  3. customthe yellow cloudy reaction mixture
  4. extractionextracted with EtOAc (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated to an oily yellow solid which
  7. customwas triturated with 5% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-82e125c3a38c418bad16b57ba4376d76
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518945B2

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