Trifluoroacetic acid → (3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone

HRID 1524923

반응식

HRID 1524923 반응식
[N:1]1[N:2]([C:6]2[C:7]([C:12]([N:14]3[CH2:18][CH:17]4[CH2:19][N:20](C(OC(C)(C)C)=O)[CH2:21][CH:16]4[CH2:15]3)=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=2)[N:3]=[CH:4][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[N:2]([C:6]2[C:7]([C:12]([N:14]3[CH2:18][CH:17]4[CH:16]([CH2:21][NH:20][CH2:19]4)[CH2:15]3)=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=2)[N:3]=[CH:4][CH:5]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86669169tert-Butyl 5-(3-(2H-1,2,3-triazol-2-yl)picolinoyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

생성물 1

HCID 67116358(3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone수율 84.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl 5-(3-(2H-1,2,3-triazol-2-yl)picolinoyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (491 mg, 1.28 mmol) in DCM (6 mL) was added TFA (3 mL). After stirring for 2 h at room temperature the reaction was complete and concentrated in vacuo. The TFA salt was purified on a Prep Agilent system with a XBridge C18 OBD 50×100 mm column eluting with 5 to 99% 0.05% NH4OH in H2O/ACN over 17 min to afford (3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone as a white solid (306 mg, 84%). MS (ESI) mass calculated for C14H16N6O, 284.14; m/z found, 285.0.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe TFA salt was purified on a Prep Agilent system with a XBridge C18 OBD 50×100 mm column
  3. washeluting with 5 to 99% 0.05% NH4OH in H2O/ACN over 17 min

출처 및 근거

ORD 기록
ord-4fb60e42842a4158a0a72fe079c050ee
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079911B2

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