Triethylamine → 3,3,3-trifluoro-N-methyl-N-[[5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octan-8-yl]sulfonyl]propanamide

HRID 589978ノート

反応式

HRID 589978 の反応式
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].C(Cl)(=O)C(Cl)=O.C(OC([N:22]1[C:26]2[N:27]=[CH:28][N:29]=[C:30]([N:31]3[CH2:38][C:35]4([CH2:37][CH2:36]4)[N:34]([S:39](=[O:43])(=[O:42])[NH:40][CH3:41])[CH2:33][CH2:32]3)[C:25]=2[CH:24]=[CH:23]1)=O)(C)(C)C.CCN(CC)CC>C(Cl)Cl.O.CN(C=O)C>[F:1][C:2]([F:8])([F:7])[CH2:3][C:4]([N:40]([CH3:41])[S:39]([N:34]1[C:35]2([CH2:37][CH2:36]2)[CH2:38][N:31]([C:30]2[C:25]3[CH:24]=[CH:23][NH:22][C:26]=3[N:27]=[CH:28][N:29]=2)[CH2:32][CH2:33]1)(=[O:42])=[O:43])=[O:5]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27779723,3,3-Trifluoropropionic acidHCID 682959194-(4-Methylsulfamoyl-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

生成物 1

HCID 574114103,3,3-trifluoro-N-methyl-N-[[5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octan-8-yl]sulfonyl]propanamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

3,3,3-trifluoropropanoic acid (0.24 mmol) was dissolved in dry DCM (0.5 mL) in a 4 mL vial, added oxalyl chloride (0.24 mmol) and a catalytic amount of DMF. Stirred at rt for 1 h and added to a mixture of intermediate 4 (0.05 mmol) and Et3N (0.47 mmol) in dry DCM (0.5 mL). Stirred at rt for 16 h. Reaction mixture filtered through a syringe filter, added TFA (1 mL) and stirred at rt for 15 min. Reaction mixture added H2O (5 mL) and extracted with DCM (3×5 mL). The organic phase was dried (Na2SO4), filtered, concentrated in vacuo and redissolved in DMSO (1 mL). The pure compound was obtained by standard preparative HPLC purification.

後処理

  1. stirringStirred at rt for 16 h
  2. customReaction mixture
  3. filtrationfiltered through a syringe
  4. filtrationfilter
  5. additionadded TFA (1 mL)
  6. stirringstirred at rt for 15 min
  7. customReaction mixture
  8. extractionextracted with DCM (3×5 mL)
  9. dry with materialThe organic phase was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. dissolutionredissolved in DMSO (1 mL)
  13. customThe pure compound was obtained by standard preparative HPLC purification

出典と根拠

ORDレコード
ord-55de59ea82b7494cbb9892780d8c35da
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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