Acetyl chloride → N[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3yl]acetamide

HRID 8788

반응식

HRID 8788 반응식
[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](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].[C:32](Cl)(=[O:34])[CH3:33].C(N(CC)CC)C>C(Cl)Cl>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[C:10]3[C:2]([NH:1][C:32](=[O:34])[CH3:33])=[C:3]([C:26](=[O:31])[C:27]([CH3:28])([CH3:30])[CH3:29])[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:12][CH:13]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 102542841-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)-2,2-dimethylpropan-1-one

생성물 1

HCID 10481643N[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3yl]acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 0.050 g (0.106 mmol) of the product from Example 17 in CH2Cl2 (1 mL) at 0° C. was treated with acetyl chloride (8 μL; 0.106 mmol) followed by triethylamine (15 μL; 0.106 mmol). After the addition, the reaction mixture was warmed to RT and stirred for 1 hour. 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 20% ethyl acetate-hexane gradient) gave the title compound. HPLC/MS: 515.0 (M+1), 517.0 (M+3); Rt=4.94 min.

후처리

  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 20% ethyl acetate-hexane gradient)

출처 및 근거

ORD 기록
ord-abf83597ba6e4559a8be72219905d54c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

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