N-Methyl-tert-butylamine → 2-(3-(tert-butyl(methyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056037Notes

Reaction equation

HRID 1056037 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][NH:23][C:24]([CH3:27])([CH3:26])[CH3:25]>>[C:24]([N:23]([CH3:22])[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)([CH3:27])([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 84552N-Methyl-tert-butylamineHCID 897843702-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 717312782-(3-(tert-butyl(methyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneYield 72%

Conditions

Temperature
120 °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; 73 mg, 0.259 mmol) and N,2-dimethylpropan-2-amine (93 μl, 0.776 mmol, Fluka) and heating at 120° C. for 7 h. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-(3-(tert-butyl(methyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (72% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (s, 9H) 2.87 (t, J=6.94 Hz, 2H) 3.26 (s, 3H) 3.44 (td, J=6.80, 2.45 Hz, 2H) 6.95 (br. s., 1H) 7.07 (d, J=2.35 Hz, 1 H) 7.44 (t, J=7.82 Hz, 1H) 7.70 (dd, J=8.02, 1.17 Hz, 1H) 7.90 (dd, J=7.43, 1.37 Hz, 1H) 8.75 (s, 1H) 11.78 (br. s., 1H). MS (ESI, pos. ion) m/z: 350.1 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 4% MeOH/DCM)

Sources & evidence

ORD record
ord-06f81f6d15a047bea08c9ed711408c28
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…