2,2-Dimethylpiperazine → 2-(3-(3,3-dimethylpiperazin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056036Notes

Reaction equation

HRID 1056036 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]1([CH3:29])[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>>[CH3:22][C:23]1([CH3:29])[NH:24][CH2:25][CH2:26][N:27]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([N:11]=2)=[C:9]([C:12]2[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=2)[CH:8]=[CH:7][CH:6]=3)[CH2:28]1

Participants

3

Reactant 2

HCID 146641862,2-DimethylpiperazineHCID 897843702-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 897838842-(3-(3,3-dimethylpiperazin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneYield 67%

Conditions

Temperature
60 °C

Procedure

Prepared similarly to that described in Example 210 using 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 57 mg, 0.202 mmol) and 2,2-dimethylpiperazine (46.1 mg, 0.404 mmol, Chem-Impex International, Wood Dale, Ill.), heating at 60° C. for 1 h. Purification by filtration provided 2-(3-(3,3-dimethylpiperazin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (67% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13 (s, 6H) 2.87 (t, J=6.85 Hz, 2H) 2.92-2.99 (m, 2H) 3.44 (td, J=6.85, 2.15 Hz, 2H) 3.61 (s, 2H) 3.74 (t, J=4.69 Hz, 2H) 6.94 (br. s., 1H) 7.14 (d, J=2.15 Hz, 1H) 7.39 (t, J=7.82 Hz, 1H) 7.66 (d, J=6.85 Hz, 1H) 7.89 (d, J=6.46 Hz, 1H) 8.87 (s, 1H) 11.77 (br. s., 1H). MS (ESI, pos. ion) m/z: 377.1 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification
  3. filtrationby filtration

Sources & evidence

ORD record
ord-5e8fb565039a40b1919d6fcc8ca119a7
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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