Triethylamine → N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-3-[3-(2-pyridinyl)-1H-1,2,4-triazol-5-yl]propanamide

HRID 1070505ノート

反応式

HRID 1070505 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]([CH2:12][CH2:13][C:14]([OH:16])=O)[NH:9][N:8]=1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1.C(N(CC)CC)C.[OH-].[Na+]>CC(N(C)C)=O.ClCCl>[Cl:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:22][N:23]1[CH2:24][CH2:25][CH:26]([NH:29][C:14](=[O:16])[CH2:13][CH2:12][C:10]2[NH:9][N:8]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[N:11]=2)[CH2:27][CH2:28]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 223961833-[3-(2-pyridinyl)-1H-1,2,4-triazol-5-yl]propanoic acidHCID 223962061-(3,4-Dichloro-benzyl)-piperidin-4-ylamine hydrochloride

生成物 1

HCID 22396188N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-3-[3-(2-pyridinyl)-1H-1,2,4-triazol-5-yl]propanamide収率 4.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 31374Dimethylacetamide溶媒

実験手順

3-[3-(2-Pyridinyl)-1,2,4-triazol-5-yl]propanoic acid (0.218 g) in 1 ml dimethylacetamide) and N,N′-carbonyldiimidazole (0.250 g) in dichloromethane was stirred under nitrogen for 30 minutes. 1-(3,4-Dichlorobenzyl)-4-piperidinamine hydrochloride (0.316 g), and triethylamine (0.218 g) was then added and allowed to stir for 2 hours under nitrogen. 1M sodium hydroxide was added to the reaction with the resulting solution being washed three times with dichloromethane. The aqueous phase was acidified with glacial acetic acid, with the water/acetic acid being removed under reduced pressure. Water was then added and extracted three times with dichloromethane. The pooled organic phases were extracted once with water and the water removed under reduced pressure to leave a white solid. This was then triturated with diethyl ether/dichloromethane, filtered and was purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile), solvent removed to leave N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-3-[3-(2-pyridinyl)-1H-1,2,4-triazol-5-yl]propanamide (0.02 g).

後処理

  1. washbeing washed three times with dichloromethane
  2. customremoved under reduced pressure
  3. additionWater was then added
  4. extractionextracted three times with dichloromethane
  5. extractionThe pooled organic phases were extracted once with water
  6. customthe water removed under reduced pressure
  7. customto leave a white solid
  8. customThis was then triturated with diethyl ether/dichloromethane
  9. filtrationfiltered
  10. customwas purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile), solvent
  11. customremoved

出典と根拠

ORDレコード
ord-22ba026248014001b3ffa8ba7e3a3e21
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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