Water → 7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid methyl-(3-phenyl-propyl)-amide

HRID 589965ノート

反応式

HRID 589965 の反応式
C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:29])(=[O:28])[NH:26][CH3:27])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.O>CN(C=O)C>[CH3:27][N:26]([CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[S:25]([N:20]1[CH2:19][CH2:18][N:17]([C:16]2[C:11]3[CH:10]=[CH:9][NH:8][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:24][C:21]21[CH2:22][CH2:23]2)(=[O:29])=[O:28]

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 12503(3-Bromopropyl)benzeneHCID 682959194-(4-Methylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester2 回

生成物 1

HCID 682960107-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid methyl-(3-phenyl-propyl)-amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
35 °C

実験手順

4-(4-Methylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 4) (0.71 mmol) was dissolved in dry DMF (0.5 mL) and added Cs2CO3 (0.85 mmol) and (3-bromo-propyl)-benzene (0.085 mmol). Stirred at 35° C. for 1.5 h and then added H2O (2 mL). Extracted with EtOAc (3×2 mL) and the combined organic phases were concentrated in vacuo. The residual oil was treated with TFA (2 mL) at rt→45° C. for 1.5 h. The crude reaction mixture was concentrated in vacuo and redissolved in DMSO (0.5 mL). The pure compounds were obtained by standard preparative HPLC purification of the reaction mixture.

後処理

  1. extractionExtracted with EtOAc (3×2 mL)
  2. concentrationthe combined organic phases were concentrated in vacuo
  3. additionThe residual oil was treated with TFA (2 mL) at rt→45° C. for 1.5 h
  4. customThe crude reaction mixture
  5. concentrationwas concentrated in vacuo
  6. dissolutionredissolved in DMSO (0.5 mL)
  7. customThe pure compounds were obtained by standard preparative HPLC purification of the reaction mixture

出典と根拠

ORDレコード
ord-06f5e679552a426cbdcb6ab3f6925d09
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…