Ethoxalyl chloride → HCID 44380397, compound

HRID 2307273Notes

Reaction equation

HRID 2307273 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][N:10]1[C:19]1[CH:24]=[C:23]([NH2:25])[CH:22]=[C:21]([CH3:26])[N:20]=1>C1COCC1.N1C=CC=CC=1>[CH2:6]([O:5][C:3](=[O:4])[C:2]([NH:25][C:23]1[CH:22]=[C:21]([CH3:26])[N:20]=[C:19]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)[CH:24]=1)=[O:8])[CH3:7]

Participants

5

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 9878065HCID 9878065, compound

Product 1

HCID 44380397HCID 44380397, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

With ice bath cooling, a solution of ethyl chlorooxoacetate (2.0 g, 14.6 mmol) in THF (25 ml) was dropwise added to a solution of 2-(3,4-dihydro-1H-isoquinolin-2-yl)-6-methyl-pyridin-4-yl-amine (example 4) (2.9 g, 12.1 mmol) in pyridine (40 ml). The mixture was stirred at 75° C. for 1 hr, evaporated and partitioned (AcOEt/NaHCO3-solution). The organic phase was dried (Na2SO4), concentrated and crystallized yielding 3.1 g (75%) of the title compound as light brown solid. Mp. 128-129° C. (AcOEt), MS: m/e=340 (M+H+).

Workup

  1. temperatureWith ice bath cooling
  2. customevaporated
  3. custompartitioned (AcOEt/NaHCO3-solution)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customcrystallized

Sources & evidence

ORD record
ord-0dc891458fb34593bf6fc0736fcaa822
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

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