Sodium Carbonate → 7-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid (4-cyano-benzyl)-methyl-amide

HRID 589967ノート

反応式

HRID 589967 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+].BrC[C:38]1[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=1.[C:46]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C(Cl)Cl.O>[C:42]([C:41]1[CH:44]=[CH:45][C:38]([CH2:27][N:26]([CH3:46])[S:25]([N:20]2[CH2:19][CH2:18][N:17]([C:16]3[C:11]4[CH:10]=[CH:9][NH:8][C:12]=4[N:13]=[CH:14][N:15]=3)[CH2:24][C:21]32[CH2:23][CH2:22]3)(=[O:28])=[O:29])=[CH:39][CH:40]=1)#[N:43]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 869964-(Bromomethyl)benzonitrileHCID 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 867064317-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diaza-spiro[2.5]octane-4-sulfonic acid (4-cyano-benzyl)-methyl-amide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

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) (0.237 mmol) was dissolved in dry DMF (2 mL) and added Cs2CO3 (0.35 mmol) and 4-bromomethyl-benzonitrile (0.35 mmol). Stirred at rt for 16 h and then added H2O (10 mL). Extracted with EtOAc (3×10 mL) and the combined organic phases were concentrated in vacuo. Purified by flash chromatography on silica using a gradient of heptane to EtOAc as eluent. The obtained compound was treated with TFA (2 mL) at rt for 2 h. The crude reaction mixture was added sat. Na2CO3 to pH=7 and the extracted with EtOAc (3×10 mL). the combined organic phases was washes with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The pure compound was obtained by trituation using CH2Cl2.

後処理

  1. extractionExtracted with EtOAc (3×10 mL)
  2. concentrationthe combined organic phases were concentrated in vacuo
  3. customPurified by flash chromatography on silica using a gradient of heptane to EtOAc as eluent
  4. additionThe obtained compound was treated with TFA (2 mL) at rt for 2 h
  5. customThe crude reaction mixture
  6. extractionthe extracted with EtOAc (3×10 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe pure compound was obtained by trituation

出典と根拠

ORDレコード
ord-28db3ea54c484346882767c6827976cf
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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