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

HRID 630850ノート

反応式

HRID 630850 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, redissloved 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. washwashed with MeOH (50 mL)
  4. washThe product was eluted with 2M NH3 in MeOH
  5. concentrationconcentration in vacuo
  6. waitleft the title compound as a pale yellow solid (225 mg, >99%)

出典と根拠

ORDレコード
ord-16dabbc8252e45e59b7c610b68f869e2
出典データセット
uspto-grants-2016_04
特許番号
US09315503B2

反応ノート

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