Toluene-p-sulphonic anhydride → HCID 178427764, compound

HRID 1163252Notes

Reaction equation

HRID 1163252 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:11]3[CH2:14][CH:13]([CH2:15][OH:16])[CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.C1(O)CCCC(O)CCC1.[C:27]1([CH3:47])[CH:32]=[CH:31][C:30]([S:33]([O:36][S:37]([C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)(=[O:39])=[O:38])(=[O:35])=[O:34])=[CH:29][CH:28]=1.CCN(C(C)C)C(C)C>ClCCl>[C:27]1([CH3:47])[CH:32]=[CH:31][C:30]([S:33]([O:16][CH2:15][C@H:13]2[CH2:12][C@@H:11]([C:8]3[N:4]4[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]4=[CH:10][N:9]=3)[CH2:14]2)(=[O:35])=[O:34])=[CH:29][CH:28]=1.[C:43]1([CH3:46])[CH:42]=[CH:41][C:40]([S:37]([O:36][CH2:15][C@H:13]2[CH2:14][C@H:11]([C:8]3[N:4]4[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]4=[CH:10][N:9]=3)[CH2:12]2)(=[O:38])=[O:39])=[CH:45][CH:44]=1

Participants

7

Reactant 4

HCID 77773Toluene-p-sulphonic anhydrideHCID 81531DiisopropylethylamineHCID 90092cis-Cyclooctane-1,5-diolHCID 57681011(3-(8-Chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutyl)methanol

Product 2

HCID 178427764HCID 178427764, compoundHCID 178427765HCID 178427765, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

cis-3-(8-Chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutylmethyl toluene-4-sulfonate and trans-3-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutylmethyl toluene-4-sulfonate were prepared as follows: To a solution of [3-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutyl]methanol (˜5:1 mixture of cis- and trans-isomers, contaminated with unknown amount of cyclooctane-1,5-diol from the previous reaction, 118.8 mg, 0.5 mmol) and p-toluenesulfonic anhydride (244.8 mg, 0.75 mmol) in dichloromethane (2.0 mL) was added i-Pr2NEt (0.26 mL, 1.5 mmol). The resulting mixture was stirred at rt for 15 h. Solvents were removed and the residue was purified by silica gel chromatography (hexanes/EtOAc:4/1 to 1/1) to afford the respective cis- and trans-title compounds:

Workup

  1. customSolvents were removed
  2. customthe residue was purified by silica gel chromatography (hexanes/EtOAc:4/1 to 1/1)
  3. customto afford the respective cis- and trans-title compounds

Sources & evidence

ORD record
ord-ab165545bb974741a36947278d5e7286
Source dataset
uspto-grants-2010_10
Patent number
US07820662B2

Reaction notes

Loading…