Tert-Butylamine → N-tert-butyl-N'-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide

HRID 984431Notes

Reaction equation

HRID 984431 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:19])[C:16]([OH:18])=O)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1.[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[C:20]([NH:24][C:16](=[O:18])[C:15]([NH:14][C:5]1[CH:6]=[CH:7][C:8]([C:9]2[O:13][CH:12]=[N:11][CH:10]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:19])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22058527N-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamic acid

Product 1

HCID 9797026N-tert-butyl-N'-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamideYield 34.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 26 mg (0.1 mmol) of N-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamic acid, 15 mg (0.2 mmol) of tertiary butylamine, 28 mg (0.15 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 15 mg (0.11 mmol) of 1-hydroxy-7-azabenzotriazole in 1 ml of dimethylformamide was stirred at room temperature for 4 hours then diluted with ethyl acetate and washed with 2M hydrochloric acid, saturated sodium bicarbonate and water. The resulting solution was dried over magnesium sulphate and evaporated to dryness. The residue was triturated with diethyl ether/petrol (1:1) and collected by filtration to give 11 mg of N-tert-butyl-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide as a white solid. MS: m/e 318.0 [M+H]+.

Workup

  1. washwashed with 2M hydrochloric acid, saturated sodium bicarbonate and water
  2. dry with materialThe resulting solution was dried over magnesium sulphate
  3. customevaporated to dryness
  4. customThe residue was triturated with diethyl ether/petrol (1:1)
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-060587fcccae4b02bbbc147c6ef7dfd5
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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