Water → Tert-butyl 4-[8-(tert-butoxycarbonylsulfamoyl)-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate

HRID 589959노트

반응식

HRID 589959 반응식
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:17][C:14]3([CH2:16][CH2:15]3)[N:13]([S:18]([NH2:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)=[N:3][CH:2]=1.[C:22]([O-:25])([O-:24])=O.[Cs+].[Cs+].[O:28](C(OC(C)(C)C)=O)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=O.O>CN(C=O)C>[C:5]([O:24][C:22]([NH:21][S:18]([N:13]1[C:14]2([CH2:16][CH2:15]2)[CH2:17][N:10]([C:4]2[C:5]3[CH:9]=[CH:8][N:7]([C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:28])[C:6]=3[N:1]=[CH:2][N:3]=2)[CH2:11][CH2:12]1)(=[O:20])=[O:19])=[O:25])([CH3:9])([CH3:6])[CH3:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 90495Di-tert-butyl dicarbonateHCID 574100947-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide2회

생성물 1

HCID 68295965Tert-butyl 4-[8-(tert-butoxycarbonylsulfamoyl)-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide (intermediate 1) (1.95 mmol) was dissolved in dry DMF (15 ml), added Cs2CO3 (4.29 mmol), BOC2O (4.29 mmol) and stirred at rt for 16 h. The crude mixture was treated with water (150 mL) and extracted with EtOAc (3×100 mL). The combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica using EtOAc in heptane as eluent.

후처리

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined organic phases were washed with H2O (2×50 mL), brine (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography on silica

출처 및 근거

ORD 기록
ord-684782151efb44a2b30e4f105d6c5583
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233964B2

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