Hydrochloric Acid → HCID 178518659, compound

HRID 1363210Notes

Reaction equation

HRID 1363210 reaction equation
N1(C([O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([N:15]3[C:23](=[O:24])[NH:22][C:21]4[C:16]3=[N:17][C:18]([N:25]3[C:29]5[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:28]=5[N:27]=[CH:26]3)=[N:19][CH:20]=4)[CH2:11][CH2:10]2)=O)C=CN=C1.Cl.[OH-].[Na+]>CS(C)=O.CCOC(C)=O>[F:34][C:31]1[CH:32]=[CH:33][C:28]2[N:27]=[CH:26][N:25]([C:18]3[N:17]=[C:16]4[C:21]([NH:22][C:23](=[O:24])[N:15]4[C@H:12]4[CH2:11][CH2:10][C@H:9]([OH:8])[CH2:14][CH2:13]4)=[CH:20][N:19]=3)[C:29]=2[CH:30]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178525749HCID 178525749, compound

Product 1

HCID 178518659HCID 178518659, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A solution of trans-4-(2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-7,8-dihydropurin-9-yl)cyclohexyl 1H-imidazole-1-carboxylate (30 mg) in DMSO (5 ml) was treated with concentrated HCl (1 ml). The mixture was heated at 50° C. for 3 hours. The mixture was diluted with EtOAc and made basic with 3N NaOH (10 ml) The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated to provide 20 mg of the title compound. 1H-NMR (300 MHz, CD3OD) δ 10.5 (s, 1H), 8.8 (dd, 1H), 8.6 (s, 1H), 8.1 (dd, 1H), 7.7 (td, 1H), 4.6 (m, 1H), 4.7 (m, 1H), 4.0 (m, 1H), 2.7 (m, 2H), 2.3 (m, 2H), 2.1 (m, 2H), 1.7 (m, 2H).

Workup

  1. washwas washed three times with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8016940e9ef4983bd63ec6ec631d529
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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