Water → {Methyl-[7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonyl]-amino}-acetic acid methyl ester

HRID 589966ノート

反応式

HRID 589966 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+].[CH3:36][O:37][C:38](=[O:41])[CH2:39]Cl.O>CN(C=O)C>[CH3:36][O:37][C:38](=[O:41])[CH2:39][N:26]([CH3:27])[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:28])=[O:29]

参加物

6

反応物 4

HCID 962WaterHCID 7295Methyl chloroacetateHCID 10796Cesium carbonateHCID 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 57410569{Methyl-[7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonyl]-amino}-acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °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) (0.047 mmol) was dissolved in dry DMF (0.5 mL) and added Cs2CO3 (0.071 mmol) and chloro-acetic acid methyl ester (0.071 mmol). Stirred at 40° C. for 2 h and then added H2O (1.5 mL). Extracted with EtOAc (3×1 mL) and the combined organic phases were washed with brine (1 mL) and concentrated in vacuo. The residual oil was treated with TFA (1 mL) at rt for 1 h. The crude reaction mixture was concentrated in vacuo and redissolved in DMSO (0.5 mL). The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

後処理

  1. extractionExtracted with EtOAc (3×1 mL)
  2. washthe combined organic phases were washed with brine (1 mL)
  3. concentrationconcentrated in vacuo
  4. additionThe residual oil was treated with TFA (1 mL) at rt for 1 h
  5. customThe crude reaction mixture
  6. concentrationwas concentrated in vacuo
  7. dissolutionredissolved in DMSO (0.5 mL)
  8. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

出典と根拠

ORDレコード
ord-0f4a5bbf95aa4293b71f4ae633e5df0d
出典データセット
uspto-grants-2016_01
特許番号
US09233964B2

反応ノート

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