Potassium Carbonate → N-[4-(Aminosulfonyl)-2-chlorophenyl]-2-[3-(3-bromo-5-chlorophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]acetamide

HRID 1952364노트

반응식

HRID 1952364 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:5][C:6]1[C:7](=[O:16])[NH:8][CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13].C(=O)([O-])[O-].[K+].[K+].[NH2:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:41])[CH2:39]Br)=[C:33]([Cl:42])[CH:32]=1)(=[O:30])=[O:29]>CN(C)C=O.C(OCC)(=O)C>[NH2:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:41])[CH2:39][N:8]2[CH:9]=[CH:10][C:11]([C:12]([F:15])([F:13])[F:14])=[C:6]([O:5][C:4]3[CH:17]=[C:18]([Cl:20])[CH:19]=[C:2]([Br:1])[CH:3]=3)[C:7]2=[O:16])=[C:33]([Cl:42])[CH:32]=1)(=[O:30])=[O:29]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 584600533-(3-Bromo-5-chlorophenoxy)-4-(trifluoromethyl)pyridin-2-olHCID 59511722N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoAcetamide

생성물 1

HCID 42644877N-[4-(Aminosulfonyl)-2-chlorophenyl]-2-[3-(3-bromo-5-chlorophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]acetamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To 3-(3-bromo-5-chlorophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one (3B, 0.050 g, 0.136 mmol) and potassium carbonate (0.019 g, 0.136 mmol) suspended in dimethylformamide (1 mL) was added N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoacetamide (0.046 g, 0.136 mmol) as a solution in dimethylformamide (1 mL). The reaction mixture was allowed to stir at room temperature. After 16 hours, the reaction mixture was diluted with ethyl acetate (20 mL), washed with water (3×10 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 12 gram column, eluting with 0-5% methanol in CH2Cl2 to yield the title compound. 1H NMR (DMSO-d6) δ 10.23 (s, 1H), 8.0 (d, J=8.6 Hz, 1H), 7.96 (d, J=7.2 Hz, 1H), 7.90 (d, J=2.1 Hz, 1H), 7.75 (dd, J=8.6 Hz, J=2.1 Hz, 1H), 7.48-7.44 (m, 2H), 7.44-7.42 (m, 1H), 7.19-7.17 (m, 1H), 7.12-7.10 (m, 1H), 6.66 (d, J=7.2 Hz, 1H), 5.02 (s, 2H). HRMS (M+1)=613.913.

후처리

  1. washwashed with water (3×10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 12 gram column
  6. washeluting with 0-5% methanol in CH2Cl2

출처 및 근거

ORD 기록
ord-3b32b4eade0944f8963fec32eac5aa70
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404856B2

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