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

HRID 2376079ノート

反応式

HRID 2376079 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7f03fca069d14b36bec165ac6375b694
出典データセット
uspto-grants-2008_12
特許番号
US07465731B2

反応ノート

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