Water → HCID 57500678, compound

HRID 1919657Notes

Reaction equation

HRID 1919657 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 57500678HCID 57500678, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-6e052a93807f4c69b38e8fcbc95c7fe3
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

Loading…