Pyridine → 4-allyl-N-(3-chlorophenyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 2098374ノート

反応式

HRID 2098374 の反応式
[CH2:1]([C:4]1([C:17](=[O:26])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH2:9][CH2:8][N:7]([C:10](OC(C)(C)C)=O)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C(C1(C(O)=O)CC[N:33]([C:36](OC(C)(C)C)=O)CC1)C=C.[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(Cl)(=O)C(Cl)=O.ClC1C=C(C=CC=1)[NH2:62]>CN(C=O)C.C(Cl)Cl>[CH2:1]([C:4]1([C:17]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[O:26])[CH2:5][CH2:6][N:7]([C:10]2[C:50]3[C:48]([CH3:49])=[CH:47][NH:46][C:51]=3[N:62]=[CH:36][N:33]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

参加物

8

反応物 5

HCID 1049PyridineHCID 79323-ChloroanilineHCID 65578Oxalyl chlorideHCID 224691981-((Tert-butoxy)carbonyl)-4-(prop-2-en-1-yl)piperidine-4-carboxylic acidHCID 67036827Tert-butyl 4-allyl-4-(3-chlorophenylcarbamoyl)piperidine-1-carboxylate

生成物 1

HCID 444823884-allyl-N-(3-chlorophenyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide収率 51%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

Preparation of tert-butyl 4-allyl-4-(3-chlorophenylcarbamoyl)piperidine-1-carboxylate. Under an atmosphere of N2, 4-allyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (0.158 g, 0.586 mmol), pyridine (0.189 mL, 2.34 mmol), and DMF (3 drops) were dissolved in CH2Cl2 (10 mL) and cooled in an ice bath. To the cooled solution, oxalyl chloride (0.056 mL, 0.645 mmol) was added dropwise. The reaction was stirred for 40 min, after which time 3-chloroaniline (0.061 mL, 0.586 mmol) was added. The reaction was removed from the ice bath and stirred at room temperature overnight. The crude reaction was washed with 1 N aq. HCl and brine, dried over MgSO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (ethyl acetate/hexanes gradient) to give the title compound in 51% yield. MS (ES+) [M+H]+=379.

後処理

  1. temperaturecooled in an ice bath
  2. customThe reaction was removed from the ice bath
  3. stirringstirred at room temperature overnight
  4. customThe crude reaction
  5. washwas washed with 1 N aq. HCl and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes gradient)

出典と根拠

ORDレコード
ord-71fe0b9fe104428aa45bac164d41e9e9
出典データセット
uspto-grants-2013_05
特許番号
US08450332B2

反応ノート

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