Water → HCID 71732051, compound

HRID 1056178Notes

Reaction equation

HRID 1056178 reaction equation
[C:1]([NH:5][C:6]1[C:7]([CH3:26])=[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:27]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[C:1]([NH:5][C:6]1[C:7]([CH3:26])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[N:24]([CH3:27])[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]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71731146HCID 71731146, compound

Product 1

HCID 71732051HCID 71732051, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (193) (0.10 g, 0.28 mmol), K2CO3 (0.13 g, 0.92 mmol), and MeI (0.027 mL, 0.43 mmol) in DMF (4 mL) was stirred at 50° C. in 24 h. The reaction mixture was cooled, added H2O, the solid was filtered, dried and purified by ISCO (0-30% EtOAc/DCM) to give the title compound (35 mg, 34% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.71-7.78 (1H, m), 7.40-7.50 (1H, m), 7.35 (1H, t, J=7.6 Hz), 6.86 (1H, br. s.), 6.22 (1H, s), 5.87 (1H, s), 3.39-3.50 (3H, m), 3.11-3.21 (2H, m), 2.77 (2H, t, J=6.8 Hz), 2.51 (3H, s), 1.28 (9H, s). m/z (ESI, +ve) 364.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe solid was filtered
  3. customdried
  4. custompurified by ISCO (0-30% EtOAc/DCM)

Sources & evidence

ORD record
ord-b6b0736892c44061ad017eb3aa42acd8
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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