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

HRID 1943661

반응식

HRID 1943661 반응식
[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]

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 8471Triethylamine촉매HCID 6344Dichloromethane용매2회HCID 24386Thionyl Chloride용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1c2ed47af75544758399639936b77033
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394792B2

연결된 노트

불러오는 중…