4-Methylmorpholine → HCID 58082769, compound

HRID 2409209Notes

Reaction equation

HRID 2409209 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:10]([F:13])([F:12])[F:11])=[C:5]([C:7]([OH:9])=O)[N:6]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>ClCCl>[CH3:18][O:17][N:16]([CH3:15])[C:7]([C:5]1[N:6]=[C:2]([CH3:1])[O:3][C:4]=1[C:10]([F:13])([F:12])[F:11])=[O:9]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27756512-methyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic Acid

Product 1

HCID 58082769HCID 58082769, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-5-trifluoromethyl-oxazole-4-carboxylic acid (500 mg, 2.56 mmole) in dichloromethane (5 ml) was subsequently treated at 22° C. with N,O-dimethylhydroxylamine hydrochloride (262 mg, 2.69 mmole), N-methylmorpholine (0.29 ml, 2.69 mmole) and EDCI.HCl (516 mg, 2.69 mmole) and stirring was continued for 16 h. The mixture was washed with 1 M aqueous HCl and H2O, the organic layer was dried and evaporated to give the title compound (559 mg) as a colorless oil which was used without further purification. MS: m/z=239.0 [M]+.

Workup

  1. washThe mixture was washed with 1 M aqueous HCl and H2O
  2. customthe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-70554eb19f894d6abf7d977aa0dac2b0
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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