Tetrahydrofuran → [2-(4-Cyclobutylpiperidin-4yl-oxy)-4,5,7,8-tetrahydro-thiazolo[5,4-d]azepin-6-yl]-cyclopropyl-methanone

HRID 1402674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402674
C1([N:5]2[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)CCC1.[H-].[Na+].Br[C:15]1[S:16][C:17]2[CH2:18][CH2:19][N:20]([C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:22][C:23]=2[N:24]=1.O1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:31]1([C:8]2([O:11][C:15]3[S:16][C:17]4[CH2:18][CH2:19][N:20]([C:25]([CH:27]5[CH2:29][CH2:28]5)=[O:26])[CH2:21][CH2:22][C:23]=4[N:24]=3)[CH2:7][CH2:6][NH:5][CH2:10][CH2:9]2)[CH2:34][CH2:33][CH2:32]1

Komponenten

5

Edukt 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 581554161-Cyclobutylpiperidin-4-olHCID 66611884(2-Bromo-4,5,7,8-tetrahydro-thiazolo[5,4-d]azepin-6-yl)-cyclopropyl-methanone

Produkt 1

HCID 86719967[2-(4-Cyclobutylpiperidin-4yl-oxy)-4,5,7,8-tetrahydro-thiazolo[5,4-d]azepin-6-yl]-cyclopropyl-methanone

Versuchsvorschrift

1-Cyclobutyl-piperidin-4-ol (0.04 grams, 0.26 mmol) in tetrahydrofuran (3 mL) was treated with cooled and stirred suspension of sodium hydride (0.021 grams, 0.51 mmol) in tetrahydrofuran (8 mL) slowly over the period of 5 minutes and the reaction mixture was stirred for 2 hours at room temperature. A solution of (2-Bromo-4,5,7,8-tetrahydro-thiazolo[5,4-d]azepin-6-yl)-cyclopropyl-methanone (0.053 grams, 0.17 mmol, obtained in above step) in tetrahydrofuran (3 mL) was added drop wise over a period of 5 minutes and refluxed for 15 hours. Reaction mass was quenched onto ice cold water and the product was extracted with ethyl acetate (3×10 mL). The combined organics were washed with water followed by brine and dried over anhydrous sodium sulphate. Organic volatiles were evaporated under vacuum. The residue obtained was purified by flash chromatography (methanol/chloroform 3/97) to obtain the title compound (0.05 grams).

Aufarbeitung

  1. temperaturewith cooled
  2. stirringthe reaction mixture was stirred for 2 hours at room temperature
  3. temperaturerefluxed for 15 hours
  4. customReaction mass
  5. customwas quenched onto ice cold water
  6. extractionthe product was extracted with ethyl acetate (3×10 mL)
  7. washThe combined organics were washed with water
  8. dry with materialdried over anhydrous sodium sulphate
  9. customOrganic volatiles were evaporated under vacuum
  10. customThe residue obtained
  11. customwas purified by flash chromatography (methanol/chloroform 3/97)

Quellen und Nachweise

ORD-Eintrag
ord-8a0fcca4d2eb4d38a66893e8f77befca
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912179B2

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