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Hydrochloric Acid → 5-Amino-pyridine-2-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

HRID 1486753
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1486753
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([C:14](=[O:36])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([C:29](=[O:35])[NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:25][CH2:24]3)[CH:17]=2)=[CH:12][CH:13]=1)(C)(C)C.Cl>O1CCOCC1>[C:31]([NH:30][C:29]([CH:26]1[CH2:25][CH2:24][N:23]([CH2:22][C:18]2[CH:17]=[C:16]([NH:15][C:14]([C:11]3[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][N:10]=3)=[O:36])[CH:21]=[CH:20][CH:19]=2)[CH2:28][CH2:27]1)=[O:35])([CH3:34])([CH3:32])[CH3:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 118521983{6-[3-(4-tert-Butylcarbamoyl-piperidin-1-ylmethyl)-phenylcarbamoyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

Produkt 1

HCID 1185218555-Amino-pyridine-2-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of {6-[3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenylcarbamoyl]-pyridin-3-yl}-carbamic acid tert-butyl ester (1.21 g, 2.37 mmol) in dioxane (15 mL) is cooled to 0° C. and HCl 4M in dioxane (2.4 mL, 9.497 mmol) is added. The RM is stirred at RT for 1 h and then heated at 60° C. overnight. The red mixture is cooled down to RT and filtered. The filtercake is washed with dioxane (15 mL). The red solid residue is partitioned between DCM (15 mL) and aq.sat.NaHCO3 (15 mL). The aqueous phase is extracted twice with DCM (2×20 mL). The combined org phase are dried over MgSO4, filtered and concentrated until dryness. The title compound is obtained as a yellowish foam LC-MS C: tR=0.61 min; [M+H]+=410.4.

Aufarbeitung

  1. temperatureheated at 60° C. overnight
  2. temperatureThe red mixture is cooled down to RT
  3. filtrationfiltered
  4. washThe filtercake is washed with dioxane (15 mL)
  5. customThe red solid residue is partitioned between DCM (15 mL) and aq.sat
  6. extractionThe aqueous phase is extracted twice with DCM (2×20 mL)
  7. dry with materialThe combined org phase are dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated until dryness

Quellen und Nachweise

ORD-Eintrag
ord-d0d1b82dafc346fdb8e51ee954bbe6f7
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09428456B2

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