Pyridine → N1-(4-methoxybenzoyl)-N2-[1-(tert-butoxycarbonyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine

HRID 395695

反応式

HRID 395695 の反応式
[C:1](Cl)(Cl)=[O:2].[C:5]([O:9][C:10](N1CCC(CO)CC1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[CH3:20][O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([NH:28][C:29]2[C:30]([NH2:35])=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:27])=[CH:24][CH:23]=1.[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[O:44]1CCC[CH2:45]1>C1(C)C=CC=CC=1.C(Cl)Cl.C(OCC)(=O)C.O>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:28][C:29]2[C:30]([NH:35][C:45]([O:2][CH:1]([CH:41]3[CH2:42][CH2:43][NH:38][CH2:39][CH2:40]3)[C:10]([O:9][C:5]([CH3:6])([CH3:7])[CH3:8])=[O:11])=[O:44])=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:27])=[CH:36][CH:37]=1

参加物

10

反応物 5

HCID 1049PyridineHCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 785232N-(2-Aminophenyl)-4-methoxybenzamideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

HCID 86585753N1-(4-methoxybenzoyl)-N2-[1-(tert-butoxycarbonyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine収率 93%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1.9 M phosgene in toluene (2.0 mL) was treated with 1-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine (200 mg, 0.930 mmol). After 1 h, the mixture was concentrated in vacuo and the residue dried under high vacuum for 4 h. The residue was dissolved in methylene chloride (2.5 mL) and then added dropwise to a solution of N1-(4-methoxybenzoyl)-1,2-benzenediamine (230 mg, 0.950 mmol) and pyridine (0.4 mL) in methylene chloride (5 mL) and tetrahydrofuran (1 mL). After 16 h, the mixture was poured into a mixture of water and ethyl acetate. The organic layer was washed once with 1.0 N aqueous hydrochloric acid, once with saturated sodium chloride solution, dried (potassium carbonate), and filtered. Concentration and purification of the residue by flash chromatography (silica gel, ethyl acetate/hexanes) yielded 416 mg (93%) of the title compound.

後処理

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue dried under high vacuum for 4 h
  3. dissolutionThe residue was dissolved in methylene chloride (2.5 mL)
  4. waitAfter 16 h
  5. washThe organic layer was washed once with 1.0 N aqueous hydrochloric acid, once with saturated sodium chloride solution
  6. dry with materialdried (potassium carbonate)
  7. filtrationfiltered
  8. concentrationConcentration and purification of the residue by flash chromatography (silica gel, ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-0754f222815940268f72032513eeb72b
出典データセット
uspto-grants-2003_08
特許番号
US06605626B2

関連ノート

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