Methyl chloroformate → Methyl 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-ylcarbamate

HRID 8790

反応式

HRID 8790 の反応式
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[O:27].Cl[C:35]([O:37][CH3:38])=[O:36].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[C:10]3[C:2]([NH:1][C:35](=[O:36])[O:37][CH3:38])=[C:3]([C:26]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:27])[O:4][C:5]3=[N:6][C:7]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 9983227[3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

生成物 1

HCID 10030526Methyl 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-ylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 0.030 g (0.0607 mmol) of the product from Example 26 in CH2Cl2 (0.6 mL) at 0° C. was treated with methyl chloroformate (5 μL; 0.0607 mmol) followed by diisopropylethylamine (10 μL; 0.0607 mmol). After the addition, the reaction mixture was warmed to room temperature and stirred for 16 hours. The reaction was quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 30% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 551.9 (M+1), 553.9 (M+3); Rt=4.24 min.

後処理

  1. additionAfter the addition
  2. customThe reaction was quenched with saturated NaHCO3 solution
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  4. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by MPLC (silica gel; 0% to 30% ethyl acetate:hexane gradient)

出典と根拠

ORDレコード
ord-6b854e7dc2de4f828680e0b9d210b2fe
出典データセット
uspto-grants-2006_08
特許番号
US07091216B2

関連ノート

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