HCID 66754310, compound → HCID 66754191, compound

HRID 1642326Notes

Reaction equation

HRID 1642326 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][C:24]#[C:25][CH3:26])[C:18]([N:27]3[CH2:32][CH2:31][CH2:30][CH:29]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:28]3)=[N:17][C:16]=2[N:15]([CH3:41])[C:13]1=[O:14])=O>C(O)(=O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][C:24]#[C:25][CH3:26])[C:18]([N:27]3[CH2:32][CH2:31][CH2:30][CH:29]([NH:33][C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:28]3)=[N:17][C:16]=2[N:15]([CH3:41])[C:13]1=[O:14]

Participants

3

Reactant 1

HCID 66754310HCID 66754310, compound

Product 1

HCID 66754191HCID 66754191, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

350 mg of 1-[(2-amino-phenylaminocarbonyl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine are refluxed in 3 ml glacial acetic acid for two hours. Then the reaction mixture is evaporated down, the flask residue is combined with 5 ml of 1 M sodium hydroxide solution and washed with methylene chloride. Then the aqueous phase is acidified with 1 M hydrochloric acid and extracted with methylene chloride. The combined extracts are evaporated down and chromatographed through a silica gel column with cyclohexane/ethyl acetate/methanol (6:4:0 to 5:4:1) as eluant.

Workup

  1. customThen the reaction mixture is evaporated down
  2. washwashed with methylene chloride
  3. extractionextracted with methylene chloride
  4. customThe combined extracts are evaporated down
  5. customchromatographed through a silica gel column with cyclohexane/ethyl acetate/methanol (6:4:0 to 5:4:1) as eluant

Sources & evidence

ORD record
ord-51c4caf614d44ff397537d8170a86582
Source dataset
uspto-grants-2012_02
Patent number
US08119648B2

Reaction notes

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