Methylamine → HCID 89784318, compound

HRID 1056079Notes

Reaction equation

HRID 1056079 reaction equation
F[C:2]1[C:3]([CH3:23])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH:18]([CH3:21])[CH2:17][NH:16][C:15](=[O:22])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[CH3:24][NH2:25]>CS(C)=O.O>[CH3:21][CH:18]1[CH2:17][NH:16][C:15](=[O:22])[C:14]2[CH:13]=[C:12]([C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[N:11]=[C:2]([NH:25][CH3:24])[C:3]([CH3:23])=[N:4]4)[NH:20][C:19]1=2

Participants

5

Reactant 2

HCID 6329MethylamineHCID 89783714HCID 89783714, compound

Product 1

HCID 89784318HCID 89784318, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of rac-2-(3-fluoro-2-methylquinoxalin-5-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 156; 32.7 mg, 0.105 mmol) and methylamine (2.0M in THF; 0.158 mL, 0.316 mmol) in DMSO (0.8 mL) was stirred under argon in a sealed flask at 25° C. for 10 min, then at 60° C. for 1 h. The reaction was cooled to 25° C. and diluted with water (10 mL). The precipitated solid was collected by vacuum filtration, washed with water (2×5 mL), and dried in vacuo to provide rac-7-methyl-2-(2-methyl-3-(methylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (21.0 mg, 0.065 mmol, 62% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.24 (1H, br. s.), 7.93 (1H, d, J=7.4 Hz), 7.57 (1H, d, J=7.8 Hz), 7.45 (1H, d, J=4.3 Hz), 7.32 (1H, t, J=7.8 Hz), 7.04 (1H, s), 6.99 (1H, br. s.), 3.43 (1H, dt, J=11.0, 4.0 Hz), 3.09-3.21 (2H, m), 3.07 (3H, s), 2.52 (3H, s), 1.30 (3H, d, J=6.5 Hz). m/z (ESI, +ve) 322.1 (M+H)+.

Workup

  1. filtrationThe precipitated solid was collected by vacuum filtration
  2. washwashed with water (2×5 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a686dc274e334413824862ab242b274b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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