Trifluoroacetic acid → 2-(2-amino-3-(tert-butylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056163노트

반응식

HRID 1056163 반응식
[C:1]([NH:5][C:6]1[C:7]([NH:26]CC2C=CC(OC)=CC=2OC)=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=[O:25])[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:26][C:7]1[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[C:16]2[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=[O:25])[C:18]=3[CH:17]=2)[N:8]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 897938422-(3-(tert-butylamino)-2-((2,4-dimethoxybenzyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

생성물 1

HCID 717315172-(2-amino-3-(tert-butylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one수율 23%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

A solution of 2-(3-(tert-butylamino)-2-((2,4-dimethoxybenzyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (304d) (40 mg, 0.08 mmol) and TFA (1.0 mL, 12.98 mmol) in DCM (1.0 mL) was stirred at 25° C. for 1 h. The reaction mixture was subsequently heated at 40° C. for 1 h. The reaction mixture was then concentrated in vacuo, and the residue was partitioned between EtOAc (50 mL) and saturated aq. NaHCO3 (30 mL). The organic layer was separated, washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-10% MeOH/DCM) furnished 2-(2-amino-3-(tert-butylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (6.4 mg, 0.018 mmol, 23% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.12 (1H, br. s.), 7.53 (1H, dd, J=7.0, 1.8 Hz), 7.19-7.22 (1H, m), 7.14-7.19 (1H, m), 6.92 (1H, br. s.), 6.90 (1H, d, J=2.0 Hz), 6.86 (2H, s), 6.33 (1H, s), 3.43 (2H, td, J=6.9, 2.2 Hz), 2.86 (2H, t, J=6.7 Hz), 1.56 (9H, s). m/z (ESI, +ve) 351.2 (M+H)+.

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was partitioned between EtOAc (50 mL) and saturated aq. NaHCO3 (30 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification of the residue (silica gel, 0-10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-6e21817f113e42f99682983fa142488c
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394297B2

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