Water → methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate

HRID 655733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655733
Cl[C:2]1[S:3][C:4]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([C:7]2[N:11]([CH3:12])[N:10]=[CH:9][N:8]=2)[N:6]=1.[Cl:17][C:18]1[C:22]([Cl:23])=[C:21]([CH3:24])[NH:20][C:19]=1[C:25]([NH:27][C@@H:28]1[CH2:33][CH2:32][NH:31][CH2:30][C@@H:29]1[O:34][CH2:35][CH:36]=[CH2:37])=[O:26].C(N(CC)C(C)C)(C)C.O>CN1CCCC1=O>[Cl:17][C:18]1[C:22]([Cl:23])=[C:21]([CH3:24])[NH:20][C:19]=1[C:25]([NH:27][C@@H:28]1[CH2:33][CH2:32][N:31]([C:2]2[S:3][C:4]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([C:7]3[N:11]([CH3:12])[N:10]=[CH:9][N:8]=3)[N:6]=2)[CH2:30][C@@H:29]1[O:34][CH2:35][CH:36]=[CH2:37])=[O:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 59208415Methyl 2-chloro-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate2×HCID 594024493,4-dichloro-5-methyl-N-[(3S,4R)-3-(prop-2-en-1-yloxy)piperidin-4-yl]-1H-pyrrole-2-carboxamide2×

Produkt 1

HCID 46234299methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl 2-chloro-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate (Intermediate 2, 77.91 mg, 3.02 mmol) was added to a solution of 3,4-dichloro-5-methyl-N-[(3S,4R)-3-(prop-2-en-1-yloxy)piperidin-4-yl]-1H-pyrrole-2-carboxamide (Intermediate 20, 100 mg, 3.02 mmol) and N,N-diisopropylethylamine (0.362 mL, 0.06 mM) in N-methyl 2-pyrrolidinone (1.5 mL) and the resulting reaction mixture was stirred overnight at 80° C. The reaction mixture was cooled to room temperature and poured into water (20 mL). The solid that formed was collected by filtration, washed with diethylether (25 mL) and dried to afford Methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate (90 mg, 70%) as solid.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. washwashed with diethylether (25 mL)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-94a92ec444fc4d4e830007335bd6d718
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071605B2

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