Methanol → 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyridazin-3-yloxy)ethoxy}pyrimidin-4-yl]benzenesulfonamide

HRID 2273노트

반응식

HRID 2273 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)=[C:19]([O:30][CH2:31][CH2:32][O:33][C:34]3[N:35]=[N:36][C:37](Cl)=[CH:38][CH:39]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CO>[C].[Pd].O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)=[C:19]([O:30][CH2:31][CH2:32][O:33][C:34]3[N:35]=[N:36][CH:37]=[CH:38][CH:39]=3)[N:18]=[CH:17][N:16]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 887MethanolHCID 8471TriethylamineHCID 196894624-tert-butyl-N-[6-{2-(6-chloropyridazin-3-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide

생성물 1

HCID 108969304-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyridazin-3-yloxy)ethoxy}pyrimidin-4-yl]benzenesulfonamide수율 78.6%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 4-tert-butyl-N-[6-{2-(6-chloropyridazin-3-yloxy)ethoxy}-5-(3-methoxyphenoxy)pyrimidin-4-yl]benzenesulfonamide (150 mg), 10% palladium-carbon (30 mg), triethylamine (52 mg), methanol (8 ml) and tetrahydrofuran (6 ml) is stirred at room temperature for five hours under hydrogen atmosphere (1 atm), and the mixture is filtered to remove the catalyst. The filtrate is concentrated to dryness under reduced pressure. The residue is treated with aqueous citric acid solution, and extracted with chloroform. The extract is washed, dried and evaporated to remove the solvent. The residue is recrystallized from ethyl acetate/diisopropyl ether to give 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyridazin-3-yloxy)ethoxy}pyrimidin-4-yl]benzenesulfonamide (111 mg) as crystals.

후처리

  1. filtrationthe mixture is filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure
  4. additionThe residue is treated with aqueous citric acid solution
  5. extractionextracted with chloroform
  6. washThe extract is washed
  7. customdried
  8. customevaporated
  9. customto remove the solvent
  10. customThe residue is recrystallized from ethyl acetate/diisopropyl ether

출처 및 근거

ORD 기록
ord-247f89c623c34222bcd61e153cb12689
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728706

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