5-Amino-1,2,4-thiadiazole → N-(4-(4-(1,2,4-thiadiazol-5-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)-3,3,3-trifluoropropanamide

HRID 390424

反応式

HRID 390424 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=2)[N:3]=1.[S:24]1[C:28]([NH2:29])=[N:27][CH:26]=[N:25]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[S:24]1[C:28]([NH:29][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][C:10]3[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=3)[N:3]=2)=[N:27][CH:26]=[N:25]1

参加物

5

反応物 3

HCID 2902745-Amino-1,2,4-thiadiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59352891N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)-3,3,3-trifluoropropanamide

生成物 1

HCID 59450317N-(4-(4-(1,2,4-thiadiazol-5-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)-3,3,3-trifluoropropanamide収率 34%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

To a round bottom flask was added N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)-3,3,3-trifluoropropanamide (350 mg, 0.9 mmol), 1,2,4-thiadiazole-5-amine (100 mg, 0.9 mmol), xanthphos (50 mg, 0.1 mmol), Pd2 dba3 (50 mg, 0.05 mmol), NaCO3 (150 mg, 1.5 mmol) and dioxane(10 cm). The mixture was flushed with nitrogen and then brought to reflux for 2 hours. The mixture was filtered, partitioned between ethylacetate and bicarbonate. The organic layer was dried with magnesium sulfate, and concentrated to an oil, which was purified by column chromatography to yield the product as a yellow solid (127 mg, 34%)

後処理

  1. customThe mixture was flushed with nitrogen
  2. temperatureto reflux for 2 hours
  3. filtrationThe mixture was filtered
  4. custompartitioned between ethylacetate and bicarbonate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated to an oil, which
  7. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-b08aecb389014c2983dc64e972c5b12a
出典データセット
uspto-grants-2013_02
特許番号
US08383633B2

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