Water → 4-(4-Sulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

HRID 589944ノート

反応式

HRID 589944 の反応式
[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([O-])([O-])=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:32]([O:31][C:29]([N:7]1[C:6]2[N:1]=[CH:2][N:3]=[C:4]([N:10]3[CH2:17][C:14]4([CH2:16][CH2:15]4)[N:13]([S:18](=[O:20])(=[O:19])[NH2:21])[CH2:12][CH2:11]3)[C:5]=2[CH:9]=[CH:8]1)=[O:28])([CH3:35])([CH3:34])[CH3:33]

参加物

6

反応物 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 amide2 回

生成物 1

HCID 682960294-(4-Sulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid amide (intermediate 1) (1.5 g, 4.86 mmol) was dissolved in dry DMF (20 ml), added Cs2CO3 (1.59 g, 4.86 mmol) and cooled to 0° C. A solution of BOC2O (1.06 g, 4.86 mmol) in dry DMF (10 mL) was added and the reaction mixture was allowed to warm up to rt 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.

後処理

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

出典と根拠

ORDレコード
ord-c5f289ecaf314a50bdcdd674babef978
出典データセット
uspto-grants-2016_01
特許番号
US09233964B2

反応ノート

読み込み中…