p-Toluenesulfonic acid → HCID 178518645, compound

HRID 600456Notes

Reaction equation

HRID 600456 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[N:6]2[C@H:21]1[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]1.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl.C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[N:6]2[C@H:21]1[CH2:22][CH2:23][C@H:24]([O:27][CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][O:29]2)[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 178518646HCID 178518646, compound

Product 1

HCID 178518645HCID 178518645, compound

Reagents, catalysts & solvents 1

HCID 21956068Chloroform tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 6-chloro-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-(trans-4-hydroxycyclohexyl)-7H-purin-8(9H)-one (0.8 mmol) and dihydropyran (15 equiv.) in anhydrous chloroform/THF (30 mL/15 mL) containing p-TsOH (0.1 equiv.) was stirred at 50° C. for 1 day (LCMS indicative of complete reaction). The reaction mixture was concentrated in vacuo and the residue purified by column chromatography on neutral alumina to give the desired product. MS (EI) m/z 487.3 (MH)+.

Workup

  1. custom(LCMS indicative of complete reaction)
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue purified by column chromatography on neutral alumina

Sources & evidence

ORD record
ord-6240b5f7efa340a79901511d892366ed
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

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