Water → HCID 66976987, compound

HRID 712195Notes

Reaction equation

HRID 712195 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Br:12])[C:5]2[O:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.C(N(CC)CC)C.[CH2:20]([N:22]=[C:23]=[O:24])[CH3:21].O>CS(C)=O.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([Br:12])[C:5]2[O:9][C:8]([NH:10][C:23]([NH:22][CH2:20][CH3:21])=[O:24])=[N:7][C:6]=2[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8022Ethyl isocyanate2×HCID 8471Triethylamine2×HCID 40236Benzoxazole, 2-amino-5,7-dibromo-

Product 1

HCID 66976987HCID 66976987, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5,7-dibromo-1,3-benzoxazol-2-amine 1(1050 mg; 3.60 mmol) in DMSO (0.7 mL) and dioxane (16 mL) was treated with triethylamine (980 mg, 9.7 mmol) and ethyl isocyanate (767 mg, 10.79 mmol). The reaction was stirred at 60° C. for 24 h. After that time an additional batch of ethyl isocyanate (400 mg, 6 mmol) and triethylamine (500 mg, 5 mmol) were added and the mixture stirred at 60° C. further 24 h. Water was then added and the solid formed was filtrated, rinsed with water and then triturated with EtOAc to give the desired product as a white-off solid (m=950 mg; yield: 73%). 1H NMR (DMSO) δ 11.25 (br s, 1H), 8.16-8.10 (m, 1H), 8.09 (s, 1H), 7.91 (s, 1H), 3.30-3.22 (m, 2H), 1.13 (t, J=7.2 Hz, 3H). ESI-MI m/z [M+H]+: 293.1. 1Prepared according to the method described in J. Pharm. Sci (1964) Vol. 53 p 538-544.

Workup

  1. stirringthe mixture stirred at 60° C. further 24 h
  2. customthe solid formed
  3. filtrationwas filtrated
  4. washrinsed with water
  5. customtriturated with EtOAc

Sources & evidence

ORD record
ord-d59c5a6b22294074b5a51779e4352488
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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