Hydrochloric Acid → 3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

HRID 2196604노트

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HRID 2196604 반응식
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[SH:7].CC(C)([O-])C.[K+].Cl[C:15]1[N:20]=[C:19]([C:21]([NH:23][C:24]2[S:28][N:27]=[C:26]([CH3:29])[N:25]=2)=[O:22])[C:18]([S:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=[CH:17][CH:16]=1.Cl>O.C(Cl)(Cl)Cl.CC(N(C)C)=O>[OH:37][C:34]1[CH:35]=[CH:36][C:31]([S:30][C:18]2[C:19]([C:21]([NH:23][C:24]3[S:28][N:27]=[C:26]([CH3:29])[N:25]=3)=[O:22])=[N:20][C:15]([S:7][C:3]3[N:2]([CH3:1])[CH:6]=[N:5][N:4]=3)=[CH:16][CH:17]=2)=[CH:32][CH:33]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 866196096-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamideHCID 178481306HCID 178481306, 화합물

생성물 1

HCID 597062523-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide수율 63.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 31374Dimethylacetamide용매

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온도
160 °C

실험 절차

20 g of 4-methyl-4H-1,2,4-triazole-3-thiol and 19 g of potassium t-butoxide were added to a dimethylacetamide (130 ml) solution of 13 g of 6-chloro-3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide, and stirred under heat at 160° C. for 8 hours. At room temperature, chloroform and water were added to it, and its pH was controlled to 3 with aqueous 1 N hydrochloric acid solution added thereto. This was extracted with chloroform, and the organic layer was washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol) to obtain 10.0 g of the entitled compound as a yellow solid.

후처리

  1. additionadded
  2. extractionThis was extracted with chloroform
  3. washthe organic layer was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol)

출처 및 근거

ORD 기록
ord-3b4e3bc0593b4f3c889d066f101fb31e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338460B2

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