Dimethylamine → HCID 58015478, compound

HRID 219286Notes

Reaction equation

HRID 219286 reaction equation
[C:1]([C:3]1[N:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:8][C:4]=1[C:5]([NH2:7])=[O:6])#[CH:2].CNC>CO>[NH4+:7].[OH-:6].[CH3:16][O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[N:11][C:3]2[CH:1]=[CH:2][NH:7][C:5](=[O:6])[C:4]=2[CH:8]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 58015512HCID 58015512, compound

Product 2

HCID 14923Ammonium HydroxideYield 1%HCID 58015478HCID 58015478, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

2-ethynyl-5-(2-methoxyethoxy)nicotinamide (2.04 g, 9 mmol) was dissolved in 1M dimethylamine (in methanol or ethanol) (46 ml, 93 mmol). The reaction was heated to 85° C. for 12 hrs. The reaction was concentrated and purified via MPLC eluting with 100% DCM to 90% DCM:10% MeOH:1% NH4OH to yield 3-(2-methoxyethoxy)-1,6-naphthyridin-5(6H)-one (0.900 g, 44% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified via MPLC
  3. washeluting with 100% DCM to 90% DCM

Sources & evidence

ORD record
ord-99dcf9f3700343ceba44d1d01a402343
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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