4-Methylmorpholine → HCID 58432036, compound

HRID 2359210Notes

Reaction equation

HRID 2359210 reaction equation
[N:1]1[N:2]([C:6]2[CH:11]=[CH:10][C:9]([CH:12]([O:16][CH3:17])[C:13]([OH:15])=O)=[CH:8][CH:7]=2)[N:3]=[CH:4][CH:5]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[CH3:34][NH:35][O:36][CH3:37].C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:3]1[N:2]([C:6]2[CH:7]=[CH:8][C:9]([CH:12]([O:16][CH3:17])[C:13]([N:35]([O:36][CH3:37])[CH3:34])=[O:15])=[CH:10][CH:11]=2)[N:1]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 584319912-(4-(2H-1,2,3-triazol-2-yl)phenyl)-2-methoxyacetic acid

Product 1

HCID 58432036HCID 58432036, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(2H-1,2,3-triazol-2-yl)phenyl)-2-methoxyacetic acid (1.19 g, 5.1 mmol in anhydr CH2Cl2 (15 ml) was added 4-methylmorpholine (1.55 g, 15.3 mmol) and it was cooled over an ice bath. Isobutylchloroformate (0.84 g, 6.12 mmol) was added and stirred for 45 min. N,O-Dimethylhydroxylamine HCl (0.746 g, 7.65 mmol) was added and the mixture was allowed to stir overnight while warming to room temp. Saturated aqueous NaHCO3 (15 ml) was added and stirred for 5 min. The organic layer was dried over Na2SO4 and evaporated to dryness. Purification by chromatography (100% EtOAc) gave 2-(4-(2H-1,2,3-triazol-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide as a white solid (0.63 g, 44% yield).

Workup

  1. temperaturewas cooled over an ice bath
  2. stirringto stir overnight
  3. stirringstirred for 5 min
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customPurification by chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-38787b279e4c4aa7ab8bce04de1bbf09
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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