Water → N-[(3S)-1-(aminosulfonyl)piperidin-3-yl]-8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide hydrochloride

HRID 64468

Reaktionsgleichung

Reaktionsgleichung von HRID 64468
[ClH:1].Cl.[CH:3]1([CH2:9][O:10][C:11]2[C:12]3[N:13]([C:17]([C:21]([NH:23][C@H:24]4[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]4)=[O:22])=[C:18]([CH3:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.N1C=CC=CC=1.[S:36](N)([NH2:39])(=[O:38])=[O:37].O>C(Cl)(Cl)Cl>[ClH:1].[NH2:39][S:36]([N:26]1[CH2:27][CH2:28][CH2:29][C@H:24]([NH:23][C:21]([C:17]2[N:13]3[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][CH:3]4[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]4)[C:12]3=[N:19][C:18]=2[CH3:20])=[O:22])[CH2:25]1)(=[O:38])=[O:37]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 82267SulfamideHCID 867134908-(cyclohexylmethoxy)-2-methyl-N-[(3S)-piperidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

Produkt 1

HCID 86713492N-[(3S)-1-(aminosulfonyl)piperidin-3-yl]-8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide hydrochlorideAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To 200 mg of 8-(cyclohexylmethoxy)-2-methyl-N-[(3S)-piperidin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride were added 5 ml of pyridine and 217 mg of sulfamide, followed by heating to reflux for 4 hours. After leaving to be cooled at room temperature, to the reaction mixture were added water and chloroform to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The obtained solid was suspended in ethyl acetate, and 120 μl of a 4 M hydrogen chloride/ethyl acetate solution was added thereto. The resulting solid was collected by filtration and dried to obtain 151 mg of N-[(3S)-1-(aminosulfonyl)piperidin-3-yl]-8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide hydrochloride.

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux for 4 hours
  3. customAfter leaving
  4. customa layer separation operation
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography
  8. addition120 μl of a 4 M hydrogen chloride/ethyl acetate solution was added
  9. filtrationThe resulting solid was collected by filtration
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-778e9505ab0e42f8a7079ffa8f9b8b1e
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447090B2

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