Cyclohexanecarboxaldehyde → ethyl (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoroacrylate

HRID 226393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226393
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.Cl.[Cl:17][C:18]1[CH:19]=[C:20](/[CH:31]=[C:32](\[F:38])/[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:21]=[N:22][C:23]=1[NH:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]1.[CH:39]1([CH:45]=O)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl.CCN(CC)CC>[Cl:17][C:18]1[CH:19]=[C:20](/[CH:31]=[C:32](\[F:38])/[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:21]=[N:22][C:23]=1[NH:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([CH2:45][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[CH2:26]1

Komponenten

8

Edukt 4

HCID 16275CyclohexanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86603683ethyl (2Z)-3-{5-chloro-6-[(3R)-3-piperidinylamino]-3-pyridinyl)-2-fluoroacrylate dihydrochloride

Produkt 1

HCID 86603697ethyl (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoroacrylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (0.56 g) was added a mixture of ethyl (2Z)-3-{5-chloro-6-[(3R)-3-piperidinylamino]-3-pyridinyl}-2-fluoroacrylate dihydrochloride (0.7 g), Et3N (0.49 mL) and cyclohexanecarboxaldehyde (0.23 mL) in CH2Cl2 (14 mL) and the mixture was stirred at ambient temperature for 20 hr. The reaction mixture was poured into a mixture of CHCl3 and aq NaHCO3. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give ethyl (2Z)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-piperidinyl]amino}-3-pyridinyl)-2-fluoroacrylate (0.74 g).

Aufarbeitung

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d8de91681f8946c4b605edde7cd54879
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557127B2

Notizen zur Reaktion

Wird geladen…