Hydrochloric Acid → 4-tert-butyl-N-{6-(3-hydroxypropyloxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

HRID 1082297

反応式

HRID 1082297 の反応式
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].[C:8]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22]2[C:27]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)=[C:26](Cl)[N:25]=[CH:24][N:23]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].Cl>>[C:8]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:22]2[C:27]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)=[C:26]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[N:25]=[CH:24][N:23]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 15391273p-t-butyl-N-[6-chloro-5-(m-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

生成物 1

HCID 196894894-tert-butyl-N-{6-(3-hydroxypropyloxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

実験手順

To 1,3-propanediol (7 ml) is added sodium hydride (60% dispersion-type, 312 mg), and thereto is added 4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (707 mg). The reaction mixture is reacted at 90° C. for two hours, and then reacted at 130° C. for one hour. The reaction solution is acidified with 10% hydrochloric acid, and extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1), and crystallized from ethyl acetate/diisopropyl ether to give 4-tert-butyl-N-{6-(3-hydroxypropyloxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (315 mg) as crystals.

後処理

  1. customThe reaction mixture is reacted at 90° C. for two hours
  2. customreacted at 130° C. for one hour
  3. extractionextracted with ethyl acetate
  4. washthe ethyl acetate layer is washed
  5. customdried
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=10:1)
  8. customcrystallized from ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-f8804cd0a77c42d3b58f2c66bcac06ac
出典データセット
uspto-grants-1996_12
特許番号
US05589478

関連ノート

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