Triethylamine → Methyl 3-[3-[3-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ureido]piperidin-1-yl]benzoate

HRID 602191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602191
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:19][CH2:18][CH2:17][CH:13](C(O)=O)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)=[O:4].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.C([N:39]([CH2:42]C)CC)C.[NH2:44][C:45]1[S:49][C:48]([C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=2)=[N:47][C:46]=1[CH3:57]>C1C=CC=CC=1.O>[Cl:56][C:53]1[CH:54]=[CH:55][C:50]([C:48]2[S:49][C:45]([NH:44][C:42](=[O:27])[NH:39][CH:13]3[CH2:17][CH2:18][CH2:19][N:11]([C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:3]([O:2][CH3:1])=[O:4])[CH2:12]3)=[C:46]([CH3:57])[N:47]=2)=[CH:51][CH:52]=1

Komponenten

7

Edukt 4

HCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azideHCID 589926191-[3-(Methoxycarbonyl)phenyl]nipecotic acidHCID 672673295-Amino-2-(4-chlorophenyl)-4-methylthiazole

Produkt 1

HCID 58992627Methyl 3-[3-[3-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ureido]piperidin-1-yl]benzoateAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

1-[3-(Methoxycarbonyl)phenyl]nipecotic acid (54.0 mg, 0.205 mmol) was suspended in benzene (4 mL). To this suspension, diphenylphosphoryl azide (0.0487 mL, 0.226 mmol) and triethylamine (0.0316 mL, 0.226 mmol) were added and the mixture was stirred for 2 hours while being refluxed. Subsequently, 5-amino-2-(4-chlorophenyl)-4-methylthiazole (46.0 mg, 0.205 mmol) and triethylamine (0.0316 mL, 0.226 mmol) were added and the mixture was further stirred for 6 hours while refluxed. Water was then added and the mixture was extracted with ethyl acetate. The extract was washed sequentially with 0.1 mol/L hydrochloric acid, a saturated aqueous sodium bicarbonate solution and brine. The washed product was dried over magnesium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=4:1->1:4) gave 43.5 mg (44%) of the desired compound as a yellow powder.

Aufarbeitung

  1. temperaturewhile being refluxed
  2. stirringthe mixture was further stirred for 6 hours
  3. temperaturewhile refluxed
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed sequentially with 0.1 mol/L hydrochloric acid
  6. dry with materialThe washed product was dried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=4:1->1:4)

Quellen und Nachweise

ORD-Eintrag
ord-2002cfafff2d46d2a42a0dfd9e64407f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902367B2

Notizen zur Reaktion

Wird geladen…