Potassium Carbonate → 6-[(6-tert-butylthiomethyl-pyridin-3-ylmethyl)-amino]-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1191119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191119
[C:1]([S:5][CH2:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]2[C:25]3[CH2:24][CH2:23][N:22](C(=O)C(F)(F)F)[CH2:21][CH2:20][C:19]=3[CH:18]=[CH:17][C:16]=2[Cl:32])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:1]([S:5][CH2:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]2[C:25]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20][C:19]=3[CH:18]=[CH:17][C:16]=2[Cl:32])=[CH:9][CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 866241646-[(6-tert-butylthiomethyl-pyridin-3-ylmethyl)-amino]-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Produkt 1

HCID 584955106-[(6-tert-butylthiomethyl-pyridin-3-ylmethyl)-amino]-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Dissolve 6-[(6-tert-butylthiomethyl-pyridin-3-ylmethyl)-amino]-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (4.46 g, 9.24 mmol) in methanol (20 mL). Add a solution of potassium carbonate (5.1 g, 37 mmol) in water (10 mL) and stir at room temperature for 12 h. Remove methanol in vacuo, dilute the residue with water, and extract the aqueous phase with DCM. Purify the crude mixture by SCX chromatography (20 g) eluting with methanol and a solution of NH4OH (40 mL) in methanol (140 mL). Concentrate in vacuo to obtain pure 6-[(6-tert-butylthiomethyl-pyridin-3-ylmethyl)-amino]-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (3.6 g, 100%). MS (APCI+) m/z: 390 (M+H)+.

Aufarbeitung

  1. extractionextract the aqueous phase with DCM
  2. customPurify the crude mixture by SCX chromatography (20 g)
  3. washeluting with methanol
  4. concentrationConcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-073cc5d3d8fc4f15923d16a75be0cc29
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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