Diisopropylcarbodiimide → HCID 68352357, compound

HRID 929436Notes

Reaction equation

HRID 929436 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[CH:18]([N:21]=[C:22]=[N:23][CH:24]([CH3:26])[CH3:25])([CH3:20])[CH3:19].C(Cl)(Cl)Cl.C[OH:32].[Na]>CN(C=O)C.C(OCC)(=O)C>[CH:18]([N:21]([C:15](=[O:17])[CH2:14][N:10]1[C:11]2[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=[CH:9]1)[C:22]([NH:23][CH:24]([CH3:26])[CH3:25])=[O:32])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 69550AcefyllineHCID 5360545SodiumHCID 21584188Chloroform methanol

Product 1

HCID 68352357HCID 68352357, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 119 mg (0.5 mmol) theophylline-7-acetic acid in 5 ml DMF was dropped for 15-20 minutes into pre-heated at 60° C. solution of 80 μl N,N′-diisopropyl carbodiimide (DIC) in 2.5 ml DMF. The mixture was subsequently heated for 4 hours at the same temperature. After cooling the solvent was evaporated in a vacuum. The residue was dissolved in minimal amount of chloroform and purified by flash chromatography on Silicagel-60A with chloroform:methanol (98:2) as eluent. The fractions with the desired product were pooled and evaporated, yielding 82 mg (44%) from the compound Th69 as a white powder. Rf=0.68 (chloroform/methanol (9/1), Rf=0.23 (ethyl acetate). The empirical formula (F.W. 365) was confirmed by the results from LC/MS. The main molecular peak was found at 365 with a second peak at 387 for the sodium salt. The m.p. of the product was 117-120° C. The 1H-NMR Spectrum (300 MHz) was consistent with the expected structure.

Workup

  1. temperatureThe mixture was subsequently heated for 4 hours at the same temperature
  2. temperatureAfter cooling the solvent
  3. customwas evaporated in a vacuum
  4. dissolutionThe residue was dissolved in minimal amount of chloroform
  5. custompurified by flash chromatography on Silicagel-60A with chloroform:methanol (98:2) as eluent
  6. customevaporated
  7. customyielding 82 mg (44%) from the compound Th69 as a white powder
  8. customresults from LC/MS
  9. customwas 117-120° C

Sources & evidence

ORD record
ord-731791e38579451f99cd9ac01c91e36a
Source dataset
uspto-grants-2016_03
Patent number
US09296691B2

Reaction notes

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