Sulfamic Acid → 5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 2191598Notes

Reaction equation

HRID 2191598 reaction equation
C(N1C=C([C:8]2[N:9]=[C:10]3[C:16]([CH:17]=[O:18])=[CH:15][N:14](COCC[Si](C)(C)C)[C:11]3=[N:12][CH:13]=2)C=N1)C.S(=O)(=O)([OH:29])N.[O-]Cl=O.[Na+].OP([O-])(O)=O.[K+]>O1CCOCC1.O>[N:9]1[CH:8]=[CH:13][N:12]=[C:11]2[NH:14][CH:15]=[C:16]([C:17]([OH:18])=[O:29])[C:10]=12

Participants

7

Reactant 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

Product 1

HCID 53580555H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f7debb0d847d4c6f9a3c386087a44ff5
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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