4-Methylmorpholine → HCID 58432036, compound

HRID 56551Notes

Reaction equation

HRID 56551 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. additionwas added
  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-b65dbf962c1d4fb89d8ebf12be94a6ee
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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