Water → HCID 57500678, 화합물

HRID 1919657노트

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HRID 1919657 반응식
O=[C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[NH:3]1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:30].O>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:30][C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[N:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 57500672HCID 57500672, 화합물

생성물 1

HCID 57500678HCID 57500678, 화합물수율 47%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
120 °C

실험 절차

Methyl 4-oxo-4,5-dihydrothiazolo[4,5-c]quinoline-7-carboxylate (1.0 eq, 0.62 g, 2.38 mmol) was suspended in toluene. DIEA (1.5 eq, 122 ul, 3.57 mmol) and POCl3 (2.3 eq, 507 ul, 5.47 mmol) were added and the mixture vigorously stirred at 120° C. for 1 hour. Water, ice and CH2Cl2 were added and the resulting emulsion filtered through celite. The organic phase was decanted and the aqueous phase further extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4 and the solvent removed in vacuo to afford methyl 4-chlorothiazolo[4,5-c]quinoline-7-carboxylate (0.31 g, 47% yield). LCMS (ES): >90% pure, m/z 279[M+1]+.

후처리

  1. filtrationthe resulting emulsion filtered through celite
  2. customThe organic phase was decanted
  3. extractionthe aqueous phase further extracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-6e052a93807f4c69b38e8fcbc95c7fe3
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168651B2

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