Hydrochloric Acid → 1,3-Di(cyclopropylmethyl)-8-(4-methoxybenzenesulphonylamino)xanthine

HRID 1654697ノート

反応式

HRID 1654697 の反応式
[H-].[Na+].[NH2:3][C:4]1[NH:12][C:11]2[C:10](=[O:13])[N:9]([CH2:14][CH:15]3[CH2:17][CH2:16]3)[C:8](=[O:18])[N:7]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[C:6]=2[N:5]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.Cl>O1CCCC1.O>[CH:15]1([CH2:14][N:9]2[C:10](=[O:13])[C:11]3[NH:12][C:4]([NH:3][S:31]([C:28]4[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=4)(=[O:33])=[O:32])=[N:5][C:6]=3[N:7]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[C:8]2=[O:18])[CH2:16][CH2:17]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 71356Cipamfylline

生成物 1

HCID 103434761,3-Di(cyclopropylmethyl)-8-(4-methoxybenzenesulphonylamino)xanthine収率 31%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (0.31 g of a 60% suspension in oil, 2.1 eq) was added to a suspension of 8-amino-1,3-di(cyclopropylmethyl)xanthine (1 g, 3.64 mmol) in tetrahydrofuran (25 ml). After 30 minutes, 4-methoxybenzenesulphonyl chloride (0.82 g, 1.1 eq) was added and stirring continued for 48 hours. The reaction mixture was poured into water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The combined organic solutions were dried (MgSO4), filtered and concentrated. The crude residue was purified by column chromatography over silica in 2-5% methanol/dichloromethane to afford 1,3-di(cyclopropylmethyl)-8-(4-methoxybenzenesulphonylamino )xanthine (0.50 g, 31%) as a white solid m.pt>200° C. (decomp.)

後処理

  1. waitcontinued for 48 hours
  2. extractionextracted into ethyl acetate
  3. dry with materialThe combined organic solutions were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by column chromatography over silica in 2-5% methanol/dichloromethane

出典と根拠

ORDレコード
ord-90478ef4c9d64ab0be5e29b52aad5b08
出典データセット
uspto-grants-1995_04
特許番号
US05409934

反応ノート

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