Triethylamine → SB-334867

HRID 1783293Notes

Reaction equation

HRID 1783293 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9](C(O)=O)[CH:8]=[CH:7][C:5]=2[N:6]=1.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[NH2:38][C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][N:47]=2)[N:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.CN(C)C=O>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([NH:16][C:19]([NH:38][C:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][N:47]=4)[N:42]=[CH:41][CH:40]=3)=[O:28])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 5893541,5-Naphthyridin-4-amineHCID 184756892-Methyl-1,3-benzoxazole-6-carboxylic acid

Product 1

HCID 6604926SB-334867

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To 2-methyl-6-benzoxazole carboxylic acid (1.060 g) in toluene (111 ml) solution, triethylamine (0.867 ml) and N,N-dimethylformamide (22 ml) were added. To this mixture, diphenyl phosphoryl azide (1.65 ml) was added and stirred at 65° C. for an hour. The reaction mixture was cooled to room temperature, added with 4-amino-1,5-naphthyridine (0.878 g), and the resulting mixture was stirred at 65° C. for another 72 hours. The cooled mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium carbonate. The organic layer was dried with magnesium sulfate and the solvent was distilled away to obtain a crude product of 1-(2-methylbenzoxazole-6-yl)-3-[1,5]naphthyridine-4-yl urea for 0.797 g. The crude product was dissolved in ethyl acetate at 60° C., added with 4N-hydrogen chloride-ethyl acetate solution and stirred on ice. The precipitated hydrochloride was filtrated, air-dried at 60° C. to obtain 840 mg of the title compound (CAS No. 249889-64-3). The structure of the obtained title compound and results from NMR measurement were as follows.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe resulting mixture was stirred at 65° C. for another 72 hours
  3. washwashed with a saturated aqueous sodium carbonate
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-399ffb68b68542eb948a6d964532f4fb
Source dataset
uspto-grants-2009_03
Patent number
US07501395B2

Reaction notes

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