Triethylamine → (E)-N-{(S)-2-[4-(4-chloro-benzoyl)-piperidin-1-yl]-1-hydroxymethyl-ethyl}-3-(5-cyano-2-methoxy-phenyl)-acrylamide

HRID 434302

反応式

HRID 434302 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:14][CH3:15])=[C:7](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)[CH:8]=1)#[N:2].C(N(CC)CC)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[NH2:46][C@H:47]([CH2:64][OH:65])[CH2:48][N:49]1[CH2:54][CH2:53][CH:52]([C:55]([C:57]2[CH:62]=[CH:61][C:60]([Cl:63])=[CH:59][CH:58]=2)=[O:56])[CH2:51][CH2:50]1>ClCCl>[Cl:63][C:60]1[CH:61]=[CH:62][C:57]([C:55]([CH:52]2[CH2:53][CH2:54][N:49]([CH2:48][C@H:47]([NH:46][C:11](=[O:13])/[CH:10]=[CH:9]/[C:7]3[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[O:14][CH3:15])[CH2:64][OH:65])[CH2:50][CH2:51]2)=[O:56])=[CH:58][CH:59]=1

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11458357HCID 11458357、化合物HCID 68809448[1-((S)-2-amino-3-hydroxy-propyl)-piperidin-4-yl]-(4-chloro-phenyl)-methanone hydrochloride

生成物 1

HCID 68809530(E)-N-{(S)-2-[4-(4-chloro-benzoyl)-piperidin-1-yl]-1-hydroxymethyl-ethyl}-3-(5-cyano-2-methoxy-phenyl)-acrylamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of (E)-3-(5-cyano-2-methoxy-phenyl)-acrylic acid (0.31 g, 1.55 mmol), triethylamine (0.2 ml, 1.55 mmol) and 2-(1H benzotriazol-1-yl)-1,1,3,3,-tetramethyluronium tetrafluoroborate (0.49 g 1.55 mmol) in dichloromethane (5 ml), is added to a solution of [1-((S)-2-amino-3-hydroxy-propyl)-piperidin-4-yl]-(4-chloro-phenyl)-methanone hydrochloride and triethylamine (0.4 ml, 3.1 mmol) in dichloromethane (5 ml), and the reaction mixture stirred at ambient temperature for 1 hour. The reaction mixture is diluted with dichloromethane (20 ml), washed successively with saturated sodium bicarbonate solution (25 ml) and brine (25 ml), then dried over magnesium sulphate. The solvent is evaporated and the crude residue purified by flash silica chromatography (methanol:dichloromethane; 5:95) to afford (E)-N-{(S)-2-[4-(4-chloro-benzoyl)-piperidin-1-yl]-1-hydroxymethyl-ethyl}-3-(5-cyano-2-methoxy-phenyl)-acrylamide. [MH]+482.2.

後処理

  1. washwashed successively with saturated sodium bicarbonate solution (25 ml) and brine (25 ml)
  2. dry with materialdried over magnesium sulphate
  3. customThe solvent is evaporated
  4. customthe crude residue purified by flash silica chromatography (methanol:dichloromethane; 5:95)

出典と根拠

ORDレコード
ord-3d9ba8ac63af487a80b82a2c3014f907
出典データセット
uspto-grants-2003_12
特許番号
US06670379B2

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