Trifluoroacetic acid → 6-Fluoro-3-(R)-pyrrolidin-3-yl-[1,2,4]triazolo[4,3-a]pyridine

HRID 1402296ノート

反応式

HRID 1402296 の反応式
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[N:17]3[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]3=[N:15][N:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:16]2[N:17]([C:13]([C@@H:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)=[N:14][N:15]=2)[CH:18]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86687137(R)-3-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 866871396-Fluoro-3-(R)-pyrrolidin-3-yl-[1,2,4]triazolo[4,3-a]pyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of Intermediate 90b (335 mg, 1.09 mmol) and TFA (0.812 mL, 10.9 mmol) in DCM (5 mL) was stirred at reflux for 45 min. The cooled solution was concentrated in vacuo, redissolved in MeOH (2 mL), applied to an SCX-2 cartridge (10 g) and washed with MeOH (50 mL). The product was eluted with 2M NH3 in MeOH; concentration in vacuo left the title compound as a pale yellow solid (225 mg, >99%). LCMS (Method 3): Rt 0.44 min, m/z 207 [MH+].

後処理

  1. temperatureat reflux for 45 min
  2. concentrationThe cooled solution was concentrated in vacuo
  3. dissolutionredissolved in MeOH (2 mL)
  4. washwashed with MeOH (50 mL)
  5. washThe product was eluted with 2M NH3 in MeOH
  6. concentrationconcentration in vacuo
  7. waitleft the title compound as a pale yellow solid (225 mg, >99%)

出典と根拠

ORDレコード
ord-a622b22dfa404f6992534e625711f53b
出典データセット
uspto-grants-2014_12
特許番号
US08907094B2

反応ノート

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