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 589978노트

반응식

HRID 589978 반응식
[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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-55de59ea82b7494cbb9892780d8c35da
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233964B2

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