Water → 4-[2-(2,4-dichlorophenyl)-5-methyl-4-({[5-(trifluoromethyl)pyridin-2-yl]amino}carbonyl)-1H-imidazol-1-yl]phenyl 3-methylbutane-1-sulfonate

HRID 1715108노트

반응식

HRID 1715108 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[C:11]([CH3:27])=[C:12]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)=[O:15])[N:13]=1.C(N(CC)CC)C.[CH3:42][CH:43]([CH3:50])[CH2:44][CH2:45][S:46](Cl)(=[O:48])=[O:47].O>ClCCl>[CH3:42][CH:43]([CH3:50])[CH2:44][CH2:45][S:46]([O:34][C:31]1[CH:30]=[CH:29][C:28]([N:10]2[C:11]([CH3:27])=[C:12]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][N:18]=3)=[O:15])[N:13]=[C:9]2[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:33][CH:32]=1)(=[O:48])=[O:47]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 129333273-Methylbutane-1-sulfonyl chlorideHCID 685074162-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)-5-methyl-N-[5-(trifluoromethyl)pyridin-2-yl]-1H-imidazole-4-carboxamide

생성물 1

HCID 115998914-[2-(2,4-dichlorophenyl)-5-methyl-4-({[5-(trifluoromethyl)pyridin-2-yl]amino}carbonyl)-1H-imidazol-1-yl]phenyl 3-methylbutane-1-sulfonate수율 46%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

2-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)-5-methyl-N-[5-(trifluoromethyl)pyridin-2-yl]-1H-imidazole-4-carboxamide, prepared as described in Ex. 13, Step 3 (139 mg, 0.27 mmol) and triethylamine (46 μl, 0.33 mmol) in dichloromethane (4.0 ml) were cooled to −78° C. 3-Methylbutane-1-sulfonyl chloride (56 mg, 0.33 mmol) was carefully added to the reaction mixture. The resulting mixture was stirred at −78° C. for 1 h, and then allowed to reach room temperature. Water was added to the reaction, and the phases were separated. The organic phase was washed with NaHCO3, brine and dried with Na2SO4. The solvent was removed under reduced pressure and separation by preparatory HPLC gave the title compound (81 mg, 46%) as a solid.

후처리

  1. customto reach room temperature
  2. customthe phases were separated
  3. washThe organic phase was washed with NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under reduced pressure and separation by preparatory HPLC

출처 및 근거

ORD 기록
ord-c625d70380e6435b8eba3dd1efc86452
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799804B2

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