Water → 2-(3-chloro-6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 245866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245866
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[N:9][C:10]=2[C:11]2[N:12]=[C:13]3[C:19]([CH:20]=[O:21])=[CH:18][N:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:14]3=[N:15][CH:16]=2)[CH:7]=1.S(=O)(=O)(O)N.[Cl:35]([O-])=O.[Na+].P([O-])(O)(O)=O.[K+].[OH2:45]>C1COCC1>[Cl:35][C:8]1[N:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]2=[C:10]([C:11]2[N:12]=[C:13]3[C:19]([C:20]([OH:21])=[O:45])=[CH:18][N:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:14]3=[N:15][CH:16]=2)[N:9]=1

Komponenten

7

Edukt 5

HCID 962Water2×HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 866779082-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

Produkt 1

HCID 712803452-(3-chloro-6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a round-bottomed flask, 2-(6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (254 mg, 0.55 mmol) was suspended in THF (10 ml) and water (2 ml). The suspension was cooled to 0° C. and sulfamic acid (324 mg, 3.33 mmol) was added. Then, a solution of sodium chlorite (80%, 88 mg, 0.78 mmol) and potassium dihydrogen phosphate (907 mg, 6.67 mmol) in water (6 ml) was added dropwise over 10 min. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was triturated with hexanes to afford 184 mg of 2-(3-chloro-6-fluoro-imidazo[1,5-a]pyridin-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a light green powder which was used without further purification.

Aufarbeitung

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was triturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f40b1d8aba2f42b7a7b0fef24c5808b7
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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