Sodium Carbonate → N-(4-(4-(1,2,4-thiadiazol-5-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)-2-chlorobenzamide

HRID 390430

反応式

HRID 390430 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[N:19]=[C:18]([Cl:20])[CH:17]=[C:16](Cl)[N:15]=2)=[CH:9][CH:8]=1)=[O:5].[S:26]1[C:30]([NH2:31])=[N:29][CH:28]=[N:27]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.CO.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].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>[S:26]1[C:30]([NH:31][C:16]2[CH:17]=[C:18]([Cl:20])[N:19]=[C:14]([S:13][C:10]3[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=4[Cl:1])=[CH:8][CH:9]=3)[N:15]=2)=[N:29][CH:28]=[N:27]1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 2902745-Amino-1,2,4-thiadiazoleHCID 594207972-Chloro-N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)benzamide

生成物 1

HCID 86644548N-(4-(4-(1,2,4-thiadiazol-5-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)-2-chlorobenzamide収率 109.5%

試薬・触媒・溶媒 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
130 °C

実験手順

2-Chloro-N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)benzamide (300 mg, 0.73 mmol), 1,2,4-thiadiazole-5-amine (74 mg, 0.73 mmol), Pd2 dba3 (36 mg), xantphos (46 mg), sodium carbonate (128 mg, 1.21 mmol) in 1,4-dioxane (10 mL) were flushed for 15 minutes with nitrogen and then heated in the microwave to 130° C. for 2 hours. The crude reaction mixture was poured in methanol, filtered through Celite and concentrated. Ethyl acetate and saturated aqueous sodium bicarbonate were added and the organic layer was dried over sodium sulfate, filtered, and concentrated to dryness to yield 380 mg N-(4-(4-(1,2,4-thiadiazol-5-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)-2-chlorobenzamide with 50-60% purity (HPLC method A, Rf=8.576 minutes) that was used as such in the next step.

後処理

  1. customThe crude reaction mixture
  2. filtrationfiltered through Celite
  3. concentrationconcentrated
  4. additionEthyl acetate and saturated aqueous sodium bicarbonate were added
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-63e53733565f43d3acf3b034b28bcf84
出典データセット
uspto-grants-2013_02
特許番号
US08383633B2

関連ノート

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