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

HRID 1056032Notes

Reaction equation

HRID 1056032 reaction equation
F[C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[CH3:22][C:23]([NH2:26])([CH3:25])[CH3:24]>CS(C)=O.C(Cl)Cl>[C:23]([NH:26][C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2)([CH3:25])([CH3:24])[CH3:22]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 897843702-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 717311442-(3-(tert-butylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneYield 25%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (210i, 75 mg, 0.266 mmol) and 2-methylpropan-2-amine (56.1 μl, 0.531 mmol; Aldrich) in DMSO (2.6 ml) was stirred at 100° C. for 1 h. The mixture was diluted with DCM (150 ml), added to a separatory funnel, and washed with saturated aq. NaHCO3 (2×100 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. The impure material was dissolved in DMSO (˜20 mg/ml) and injected (4×1.0 ml) onto a Shimadzu preparatory LC (rpHPLC: Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% MeCN/water with 0.1% TFA) before the pure fractions were combined, basicified with NaHCO3 (saturated, aq.), extracted with DCM, separated, dried over Na2SO4, and concentrated via rotary evaporation to give 2-(3-(tert-butylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (210, 25% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (s, 9H) 2.87 (t, J=6.85 Hz, 2H) 3.45 (td, J=6.85, 2.35 Hz, 2H) 6.95 (br. s., 1H) 7.07 (d, J=2.15 Hz, 1H) 7.34 (t, J=7.82 Hz, 1H) 7.58 (s, 1H) 7.61 (dd, J=7.92, 1.27 Hz, 1H) 7.90 (dd, J=7.53, 1.27 Hz, 1H) 8.38 (s, 1H) 12.13 (br. s., 1H). MS (ESI, pos. ion) m/z: 336.2 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with saturated aq. NaHCO3 (2×100 ml) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. dissolutionThe impure material was dissolved in DMSO (˜20 mg/ml)
  7. extractionextracted with DCM
  8. customseparated
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-4a2c8a42a5834137912dbbd8544f6fe1
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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