1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → ethyl 1-(1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylate

HRID 83650

反応式

HRID 83650 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([OH:12])=O.CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:43]1[CH2:48][CH2:47][CH:46]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:45][CH2:44]1>C(Cl)Cl.O.C(OCC)(=O)C>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]([N:43]1[CH2:48][CH2:47][CH:46]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:45][CH2:44]1)=[O:12]

参加物

9

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70770Ethyl 4-piperidinecarboxylateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic acid

生成物 1

HCID 68379598ethyl 1-(1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylate

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1H-benzo[d]imidazole-2-carboxylic acid, H2O (500 mg, 2.78 mmol), EDCI (1170 mg, 6.11 mmol), and 1-HYDROXYBENZOTRIAZOLE (825 mg, 6.11 mmol) were dissolved in DCM. The reaction was allowed to stir for 10 minutes before Hunig's Base (1.066 mL, 6.11 mmol) and ethyl piperidine-4-carboxylate (0.941 mL, 6.11 mmol) were added. The reaction was allowed to stir overnight at room temperature. The reaction was diluted with water and ethyl acetate. The organic phase was washed with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride solution. The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated. The resulting crude material was triturated with ethyl acetate to obtain white solid as a product. (Yield: 113 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 13.09, 7.74, 7.53, 7.36-7.20, 5.31, 4.42, 4.09, 3.48, 3.05, 2.77-2.66, 1.97, 1.69-1.50, 1.20

後処理

  1. additionwere added
  2. washThe organic phase was washed with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride solution
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude material was triturated with ethyl acetate
  7. customto obtain white solid as a product

出典と根拠

ORDレコード
ord-e1197e1bdd544ebba4deaa7ef24d5c7b
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

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