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

HRID 630850노트

반응식

HRID 630850 반응식
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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+].

후처리

  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%)

출처 및 근거

ORD 기록
ord-16dabbc8252e45e59b7c610b68f869e2
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315503B2

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