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

HRID 984432Notes

Reaction equation

HRID 984432 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[C:10]1[O:14][CH:13]=[N:12][CH:11]=1)[NH2:6].[C:15]([NH:19][C:20](=[O:24])[C:21](O)=[O:22])([CH3:18])([CH3:17])[CH3:16].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1>ClCCl>[C:15]([NH:19][C:20](=[O:24])[C:21]([NH:6][C:5]1[CH:7]=[CH:8][C:9]([C:10]2[O:14][CH:13]=[N:12][CH:11]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:22])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5187990(tert-Butylamino)(oxo)acetic acidHCID 154627323-Methoxy-4-(oxazol-5-yl)aniline

Product 1

HCID 9797026N-tert-butyl-N'-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamideYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 95 mg (0.5 mmol) of 3-methoxy-4-(5-oxazolyl)aniline, 73 mg (0.5 mmol) of N-tert-butyloxalamic acid, 134 mg (0.7 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 75 mg (0.55 mmol) of 1-hydroxy-7-azabenzotriazole in 4 ml of dichloromethane was stirred a room temperature for 18 hours. The resulting mixture was washed with 2M hydrochloric acid and saturated sodium bicarbonate, dried over magnesium sulphate and evaporated to dryness. The residue was triturated with petrol and collected by filtration to give 128 mg of N-tert-butyl-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide as a pale yellow solid. MS: 318 (M+H)+.

Workup

  1. washThe resulting mixture was washed with 2M hydrochloric acid and saturated sodium bicarbonate
  2. dry with materialdried over magnesium sulphate
  3. customevaporated to dryness
  4. customThe residue was triturated with petrol
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4836aff1aa1545d1b2b98fb7deb706d8
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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