Hydrochloric Acid → HCID 12093239, compound

HRID 1454953Notes

Reaction equation

HRID 1454953 reaction equation
Cl.[CH3:2][N:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([CH2:13][N:14]2[C:23](=[O:24])[C:22]3[N:21]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[C:20]([N:30]4[CH2:35][CH2:34][CH2:33][CH:32]([NH:36]C(OC(C)(C)C)=O)[CH2:31]4)=[N:19][C:18]=3[N:17]([CH3:44])[C:15]2=[O:16])=[CH:5][S:4]1(=[O:46])=[O:45].[OH-].[Na+]>C(Cl)Cl.O>[CH3:2][N:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([CH2:13][N:14]2[C:23](=[O:24])[C:22]3[N:21]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[C:20]([N:30]4[CH2:35][CH2:34][CH2:33][CH:32]([NH2:36])[CH2:31]4)=[N:19][C:18]=3[N:17]([CH3:44])[C:15]2=[O:16])=[CH:5][S:4]1(=[O:46])=[O:45]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12093240HCID 12093240, compound

Product 1

HCID 12093239HCID 12093239, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3.5 ml isopropanolic hydrochloric acid (5-6 M) are added to 340 mg of 1-[(1-methyl-2,2-dioxo-1H-benzo[c][1,2]thiazin-4-yl)methyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine in 15 ml methylene chloride and the reaction mixture is stirred for three hours at ambient temperature. For working up it is diluted with water and methylene chloride and combined with 18 ml 1N sodium hydroxide solution. The aqueous phase is extracted with methylene chloride and the combined organic phases are washed with water, dried over magnesium sulphate and evaporated down. The yellowish, foamy flask residue is stirred with tert.-butyl-methylether and a little diethyl ether, the light-coloured precipitate formed is suction filtered and dried at 60° C. in the drying gun.

Workup

  1. extractionThe aqueous phase is extracted with methylene chloride
  2. washthe combined organic phases are washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated down
  5. stirringThe yellowish, foamy flask residue is stirred with tert.-butyl-methylether
  6. customa little diethyl ether, the light-coloured precipitate formed
  7. filtrationfiltered
  8. customdried at 60° C. in the drying gun

Sources & evidence

ORD record
ord-e2d8a311e7884116874978afaf4e3b04
Source dataset
uspto-grants-2009_01
Patent number
US07482337B2

Reaction notes

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