2,5-Dibromoterephthalic acid → 2,5-Dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid

HRID 1943661Notes

Reaction equation

HRID 1943661 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[C:8]([Br:14])=[CH:7][C:3]=1[C:4]([OH:6])=O.BrC1C=C(C(Cl)=O)C(Br)=CC=1C(Cl)=O.[O:29]1[CH2:34][CH2:33][NH:32][C:31]2[CH:35]=[N:36][CH:37]=[CH:38][C:30]1=2>CN(C)C=O.S(Cl)(Cl)=O.ClCCl.C(N(CC)CC)C>[Br:14][C:8]1[CH:7]=[C:3]([C:4]([N:32]2[CH2:33][CH2:34][O:29][C:30]3[CH:38]=[CH:37][N:36]=[CH:35][C:31]2=3)=[O:6])[C:2]([Br:1])=[CH:10][C:9]=1[C:11]([OH:13])=[O:12]

Participants

8

Reactant 3

HCID 836902,5-Dibromoterephthalic acidHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazineHCID 229969282,5-Dibromobenzene-1,4-dicarbonyl dichloride

Product 1

HCID 446088742,5-Dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

In a 20 ml flask, 2,5-dibromo-terephthalic acid (100 mg, 0.31 mmol) and N,N-dimethyl formamide (3 drops) were dissolved in thionyl chloride (2 ml). After stirring for 2 hours at 800, the reaction mixture was cooled to room temperature and concentrated. Crude 2,5-dibromo-terephthaloic dichloride (112 mg, 0.31 mmol) was dissolved in dichloromethane (6 ml) and was added to 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (20.9 mg, 0.15 mmol) dissolved in dichloromethane (1 ml). Triethylamine (3 drops) were slowly added thereto and stirred at room temperature for 16 hours. After completion of the reaction, the residue was purified by preparative LC/Mass to obtain the target compound 23, i.e., 2,5-dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid, as white solid (23 mg, 5%).

Workup

  1. concentrationconcentrated
  2. stirringstirred at room temperature for 16 hours
  3. customAfter completion of the reaction
  4. customthe residue was purified by preparative LC/Mass

Sources & evidence

ORD record
ord-1c2ed47af75544758399639936b77033
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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