Dimethylamine → HCID 46917070, compound

HRID 2045912Notes

Reaction equation

HRID 2045912 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4].[CH3:22][NH:23][CH3:24]>C1COCC1.ClCCl>[CH3:22][N:23]([CH3:24])[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Product 1

HCID 46917070HCID 46917070, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (67 mg, 0.225 mmol) in THF (3 mL), a 2 M solution of dimethylamine in THF (0.562 mL, 1.152 mmol) was added and the reaction mixture was stirred at room temperature for 48 hrs. The reaction mixture was diluted with dichloromethane (DCM, 5 mL) and solvents evaporated to afford N2,N2-dimethyl-N1-(3-quinoxalin-2-ylphenyl)glycinamide (25 mg, 36% yield). LCMS calculated for C18H18N4O (M+H): 307.37. found 307.20. 1H-NMR (MeOD, 400 Mhz) δH: 9.50 (1H, s), 8.65 (m, 1H), 8.30-8.15 (m, 3H), 8.00-7.87 (m, 3H), 7.60-7.55 (m, 1H), 4.30 (s, 2H), 3.15 (s, 6H).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-28795001beb3433da56ccc85f15af638
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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