Sulfamic Acid → 2-(6-chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 246100노트

반응식

HRID 246100 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([CH:21]=[O:22])=[CH:19][N:18]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[C:4]([F:31])[CH:3]=1.S(=O)(=O)([OH:34])N.Cl([O-])=O.[Na+].OP([O-])(O)=O.[K+]>C1COCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([OH:34])=[O:22])=[CH:19][N:18]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[C:4]([F:31])[CH:3]=1

참가 물질

8

반응물 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 866779482-(6-chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

생성물 1

HCID 712800452-(6-chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid수율 103.1%

시약·촉매·용매 3

HCID 962Water용매3회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

2-(6-Chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (255 mg, 0.55 mmol) was dissolved in THF (8.3 ml) and water (2.8 ml). Sulfamic acid (517 mg, 5.3 mmol) was added. The reaction flask was cooled in an ice/water bath and a solution of sodium chlorite (104 mg, 1.15 mmol) and potassium phosphate monobasic (1.45 g, 10.6 mmol) in water (8 ml) was slowly added. After 1 h the reaction mixture was poured into ethyl acetate and water. The layers were separated and the aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with water and sodium chloride solution, and dried over sodium sulfate. Evaporation of the solvent gave 270 mg of 2-(6-chloro-4-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a light yellow solid. (M+H)+=476.

후처리

  1. temperatureThe reaction flask was cooled in an ice/water bath
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted once more with ethyl acetate
  4. washThe combined organic layers were washed with water and sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-977e78ca05814dedb4d35600e911bbca
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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