Triethylamine → HCID 53404828, compound

HRID 2220716Notes

Reaction equation

HRID 2220716 reaction equation
O.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=O)[N:3]=1.Cl.[CH3:16][O:17][NH:18][CH3:19].C(N(CC)CC)C.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C(#N)C>[CH3:16][O:17][N:18]([CH3:19])[C:12]([C:4]1[N:3]=[CH:2][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27367043-Isoquinolinecarboxylic acid hydrateHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate

Product 1

HCID 53404828HCID 53404828, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 50 mL of acetonitrile was dissolved 0.49 g (2.60 mmol) of isoquinoline-3-carboxylic acid monohydrate. To this 0.28 g (2.87 mmol) of O,N-dimethyl-hydroxylamine hydrochloride, 0.4 mL (2.87 mmol) triethylamine and 0.921 g (3.13 mmol) of 4-(4,6-dimethoxy-[1,3,5]triazin-2-yl)-4-methyl-morpholin-4-ium chloride hydrate were added and stirred for 2 days and then evaporated. A mixture of dichloromethane and water was added to it and the organic layer was evaporated and purified using flash chromatography (0-20% methanol in dichloromethane). Fractions containing pure product were evaporated to yield 210 mg of the free base as a white solid. LC-MSD, m/z for C12H12N2O2 [M+H]+: 217.4, [M+Na]+: 239.4

Workup

  1. customevaporated
  2. additionA mixture of dichloromethane and water
  3. additionwas added to it
  4. customthe organic layer was evaporated
  5. custompurified
  6. additionFractions containing pure product
  7. customwere evaporated

Sources & evidence

ORD record
ord-cc8ef39bd556494a978d493cb4cb98b7
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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