Theophylline → HCID 131720202, compound

HRID 1378908Notes

Reaction equation

HRID 1378908 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[N:14]1([C:25](=[O:26])[C:24]2NC=N[C:20]=2N(C)[C:16]1=[O:17])C.[CH3:27][CH2:28][S:29][C:30]([N:32]([CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:31].C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>C(Cl)Cl>[C:16]1(=[O:17])[N:14]([N:8]2[CH:9]=[N:10][C:11]3[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]2=3)[C:25](=[O:26])[CH2:24][CH2:20]1.[CH3:27][CH2:28][S:29][C:30]([N:32]([CH2:37][CH:38]([CH3:39])[CH3:40])[CH2:33][CH:34]([CH3:35])[CH3:36])=[O:31]

Participants

6

Reactant 4

HCID 2153TheophyllineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 131720204HCID 131720204, compound

Product 1

HCID 131720202HCID 131720202, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The activation of theophylline was accomplished by dissolving theophylline-butylate (10 mg; MW 280.29; 3.57×10-5 moles) in methylene chloride (3.0 ml). A three mole excess of dicyclohexyl-carbodiimide (22 mg; MW 206.3) and a three mole excess of N-hydroxysuccinimide (12.3 mg; MW 115.09) were added, and the reaction mixture was stirred over night at room temperature. The mixture was filtered to remove dicyclohexylurea and was rotavaporated to dryness to yield ten milligrams of N-succinimidyl-theophylline-butylate (theophylline-butylate-oSu).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove dicyclohexylurea

Sources & evidence

ORD record
ord-16408aa7b3044656beede5eaae51ba1b
Source dataset
uspto-grants-1997_09
Patent number
US05670381

Reaction notes

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