Hydrochloric Acid → methyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylate

HRID 655775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655775
[Cl:1][C:2]1[C:3]([C:11]#[N:12])=[C:4]([C:8]([OH:10])=O)[NH:5][C:6]=1[CH3:7].[NH2:13][C@@H:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][C@@H:15]1[CH3:24].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.Cl>ClCCl>[Cl:1][C:2]1[C:3]([C:11]#[N:12])=[C:4]([C:8]([NH:13][C@@H:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][C@@H:15]2[CH3:24])=[O:10])[NH:5][C:6]=1[CH3:7]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58075083Methyl (3S,4R)-4-amino-3-methylpiperidine-1-carboxylate2×HCID 594025744-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylic acid2×

Produkt 1

HCID 59402504methyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-3-cyano-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 16, 2.12 g, 0.02 mol) and methyl (3S,4R)-4-amino-3-methylpiperidine-1-carboxylate (Intermediate 37, 2.0 g, 0.02 mol) in dichloromethane (200 mL) was added HOBt (1.77 g, 0.02 mol) and N-methyl morpholine (3.8 mL, 0.03 mol) and then the mixture was stirred for 1 h at room temperature. EDC HCl (3.98 g, 0.0208 mol) was added to the reaction mixture and stirred at room temperature overnight. The reaction mixture was added to 2N hydrochloric acid (200 mL). The organic layer was washed with sodium bicarbonate (200 mL), water (250 mL), and brine. The organic layer was dried over anhydrous sodium sulphate, filtered, concentrated under vacuum to get methyl (3S,4R)-4-{[(4-chloro-3-cyano-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylate 3.3 g (72%) as white solid.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. washThe organic layer was washed with sodium bicarbonate (200 mL), water (250 mL), and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3697475cfb5d493caaa689238d7b7ab5
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071605B2

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