Hydrochloric Acid → HCID 178518656, compound

HRID 1363206Notes

Reaction equation

HRID 1363206 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]=[CH:31][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>CS(C)=O.CCOC(C)=O>[N:25]1([C:18]2[N:17]=[C:16]3[C:21]([NH:22][C:23](=[O:24])[N:15]3[C@H:12]3[CH2:11][CH2:10][C@H:9]([OH:8])[CH2:14][CH2:13]3)=[CH:20][N:19]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[CH:26]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178525748HCID 178525748, compound

Product 1

HCID 178518656HCID 178518656, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

trans-4-(2-(1H-benzo[d]imidazol-1-yl)-8-oxo-7,8-dihydropurin-9-yl)cyclohexyl 1H-imidazole-1-carboxylate (30 mg) was dissolved in DMSO (6 mL) and treated with 1N HCl (5 ml) at 50° C. for 3 hours. The mixture was diluted with EtOAc and washed with brine three times. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to obtain 16 mg of the title compound. 1H-NMR (300 MHz, CDCl3) δ 10.0 (s, 1H), 8.9 (dd, 1H), 8.2 (s, 1H), 7.9 (dd, 1H), 7.6 (dd, 2H), 4.4 (m, 1H), 4.1 (s, 1H), 2.9 (m, 2H), 2.0 (m, 2H), 1.6 (m, 4H).

Workup

  1. washwashed with brine three times
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c69bc70ab5fd4bd1a0f96dc39d994590
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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