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

HRID 390430

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HRID 390430 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 887Methanol용매HCID 312751,4-Dioxane용매

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63e53733565f43d3acf3b034b28bcf84
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383633B2

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