Ethanol → HCID 44200044, compound

HRID 2061185Notes

Reaction equation

HRID 2061185 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([NH:20]/[C:21](/[NH2:24])=[N:22]/[OH:23])[CH:16]=[CH:17][C:18]=2[CH3:19])[C:3]1=[O:25].[S:26]1[CH:30]=[CH:29][N:28]=[C:27]1[C:31](Cl)=O.C(O)C>C1COCC1>[S:26]1[CH:30]=[CH:29][N:28]=[C:27]1[C:31]1[O:23][N:22]=[C:21]([NH:20][C:15]2[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([C:4]3[C:3](=[O:25])[N:2]([CH3:1])[C:11]4[C:6]([CH:5]=3)=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=4)[CH:14]=2)[N:24]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 27952111,3-Thiazole-2-carbonyl chlorideHCID 178422078HCID 178422078, compound

Product 1

HCID 44200044HCID 44200044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 17 (0.1 mmol) in THF (1 mL) was added thiazole-2-carbonyl chloride (0.1 mmol). The reaction mixture was stirred at rt for 30 min. Then ethanol (1 mL) was added and heated at reflux for 3 h. After filtration, the mixture was purified by preparative LC/MS to give 3-(5-(5-(thiazol-2-yl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (A9) MS m/z 431.1 (M+1).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. filtrationAfter filtration
  4. customthe mixture was purified by preparative LC/MS

Sources & evidence

ORD record
ord-627b9890c6e94b8b95b88f06c6e02acf
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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