Sodium Bicarbonate → N-(1-dimethoxymethyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2methylsulfanyl-acetamide

HRID 1962890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1962890
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]1([CH:22]=[O:23])[CH2:21][CH2:20][CH2:19]1)=[O:16])=[CH:8][CH:7]=2)#[CH:2].C1(C)C=CC=CC=1.C1C[O:36][CH2:35]C1.[C:38]([O-])(O)=O.[Na+]>CO>[CH3:38][O:23][CH:22]([O:36][CH3:35])[C:18]1([NH:17][C:15](=[O:16])[CH:14]([O:13][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:12]3)[S:24][CH3:25])[CH2:21][CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 22635083Tetrahydrofuran tolueneHCID 595654712-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide

Produkt 1

HCID 59565272N-(1-dimethoxymethyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2methylsulfanyl-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide (180 mg) from Example 12f, Step 2 described above in a 10/1 mixture of toluene/THF (11 ml) p-toluene sulphonic acid (4 mg) was added followed by MeOH (1.10 ml), at room temperature. The mixture was stirred at 50° C. overnight and 60° C. during 6 hrs, then after cooling to room temperature poured into aq NaHCO3 soln and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate) to give N-(1-dimethoxymethyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2methylsulfanyl-acetamide as white solid. 1H NMR (CDCl3) δ ppm: 8.84 (1H, d); 8.19 (1H, d); 8.05 (1H, d); 7.46 (1H, dd); 7.23 (1H, d); 6.86 (1H, br s); 5.62 (1H, s); 4.57 (1H, s); 3.51 (3H, s); 3.47 (3H, s); 3.28 (1H, s); 2.47-2.21 (4H, m); 2.21 (3H, 5); 2.01-1.73 (2H, m).

Aufarbeitung

  1. additionwas added
  2. temperatureafter cooling to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulphate anhydrous
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-31751f19c05347bb8ca4b2d0b8471d98
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415272B2

Notizen zur Reaktion

Wird geladen…