Sulfamic Acid → 2-(1-((1-(tert-Butoxycarbonyl)azetidin-3-yl)methyl)-6-fluoro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 246526노트

반응식

HRID 246526 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:23]3[N:24]=[C:25]4[C:31]([CH:32]=[O:33])=[CH:30][N:29]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:26]4=[N:27][CH:28]=3)=[N:7][N:8]2[CH2:11][CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)=[CH:4][CH:3]=1.S(=O)(=O)([OH:44])N.Cl([O-])=O.[Na+].P([O-])(O)(O)=O.[K+]>O1CCOCC1.O>[C:19]([O:18][C:16]([N:14]1[CH2:13][CH:12]([CH2:11][N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=3)[C:6]([C:23]3[N:24]=[C:25]4[C:31]([C:32]([OH:44])=[O:33])=[CH:30][N:29]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:26]4=[N:27][CH:28]=3)=[N:7]2)[CH2:15]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

참가 물질

7

반응물 4

HCID 5987Sulfamic AcidHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 86677984tert-butyl 3-((6-fluoro-3-(7-formyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1H-indazol-1-yl)methyl)azetidine-1-carboxylate

생성물 1

HCID 712801702-(1-((1-(tert-Butoxycarbonyl)azetidin-3-yl)methyl)-6-fluoro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of tert-butyl 3-((6-fluoro-3-(7-formyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)-1H-indazol-1-yl)methyl)azetidine-1-carboxylate (160 mg, 276 μmol) and sulfamic acid (161 mg, 1.65 mmol) in dioxane (5 mL) and water (2 mL), cooled to 0° C., was added a solution of sodium chlorite (32.4 mg, 358 μmol) and potassium dihydrogen phosphate (450 mg, 3.31 mmol) in water (3 mL) dropwise. The mixture was warmed to room temperature. After 2.5 h, the mixture was partitioned between ethyl acetate and water and the organic phase separated and washed with water then dried and concentrated in vacuo. A quantitative yield was assumed and the crude residue used directly in the next step without further purification.

후처리

  1. customthe mixture was partitioned between ethyl acetate and water
  2. customthe organic phase separated
  3. washwashed with water
  4. customthen dried
  5. concentrationconcentrated in vacuo
  6. customthe crude residue used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-fc20b63ae500462e909e01a82183861c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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