Triethylamine → Cis-N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxamide

HRID 1070503ノート

反応式

HRID 1070503 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C@H:12]2[CH2:14][C@H:13]2[C:15]([OH:17])=O)[O:9][N:8]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[Cl:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:23][N:24]1[CH2:25][CH2:26][CH:27]([NH:30][C:15]([C@@H:13]2[CH2:14][C@@H:12]2[C:10]2[O:9][N:8]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[N:11]=2)=[O:17])[CH2:28][CH2:29]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 12018241cis-2-[3-(2-Pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxylic acidHCID 223962061-(3,4-Dichloro-benzyl)-piperidin-4-ylamine hydrochloride

生成物 1

HCID 68886716Cis-N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxamide収率 19%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Cis-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxylic acid (0.139 g) and N,N′-carbonyldiimidazole (0.110 g) in dichloromethane was stirred under nitrogen for 1 hour. 1-(3,4-dichlorobenzyl)-4-piperidinamine hydrochloride (0.198 g), and triethylamine (0.121 g) was then added and allowed to stir for 24 hours under nitrogen. Saturated sodium hydrogen carbonate was added to the reaction with the resulting solution being extracted three times with dichloromethane. The pooled organic phases were washed once with water, once with brine, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to leave an oil. This oil was purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile). The solvent was removed under reduced pressure to leave Cis-N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxamide (0.054 g) as a white solid.

後処理

  1. extractionbeing extracted three times with dichloromethane
  2. washThe pooled organic phases were washed once with water, once with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto leave an oil
  7. customThis oil was purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile)
  8. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-ade4cc67b45f4d918fc0514a00e8c663
出典データセット
uspto-grants-2005_06
特許番号
US06903085B1

反応ノート

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