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

HRID 226393노트

반응식

HRID 226393 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d8de91681f8946c4b605edde7cd54879
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557127B2

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