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

HRID 1654697Notes

Reaction equation

HRID 1654697 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.)

Workup

  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

Sources & evidence

ORD record
ord-90478ef4c9d64ab0be5e29b52aad5b08
Source dataset
uspto-grants-1995_04
Patent number
US05409934

Reaction notes

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