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

HRID 2191598ノート

反応式

HRID 2191598 の反応式
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

参加物

7

反応物 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-carbaldehyde

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f7debb0d847d4c6f9a3c386087a44ff5
出典データセット
uspto-grants-2012_12
特許番号
US08329699B2

反応ノート

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