Triethylamine → 2-Chloromethyl-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamide

HRID 337408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337408
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1.[NH2:12][C:13]1[S:14][C:15]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[C:16]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:12][C:13]2[S:14][C:15]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[C:16]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[O:9])=[CH:5][N:4]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 149805376-(Chloromethyl)nicotinic acidHCID 231441582-Amino-4-(2-furyl)-5-morpholinothiazole

Produkt 1

HCID 231442482-Chloromethyl-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-(Chloromethyl)nicotinic acid (172 mg, 1.00 mmol) obtained in Step 1, 2-amino-4-(2-furyl)-5-morpholinothiazole (251 mg, 1.00 mmol) obtained in Step 1 of Example 29 and PyBOP (572 mg, 1.10 mmol) were dissolved in DMF (4 mL), and triethylamine (0.307 mL, 2.20 mmol) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under the reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:3) to afford the entitled Compound 36 (194 mg, 48%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under the reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-c6dd12a907d64146a3a7ef058ccba58e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889718B2

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