Trifluoromethanesulfonic anhydride → HCID 90224123, compound

HRID 2201263Notes

Reaction equation

HRID 2201263 reaction equation
[N-:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Na+].[Cl:7][C:8]1[O:12][C:11]([CH:13]2[C:18]3=[C:19]4[N:31]([CH3:32])[C:30](=[O:33])[N:29]([CH3:34])[C:28](=[O:35])[C:20]4=[C:21]([C:22]4[S:23][CH:24]=[C:25]([CH3:27])[N:26]=4)[N:17]3[CH2:16][CH:15]([CH2:36]O)[S:14]2)=[CH:10][CH:9]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[N:1]1([CH2:36][C@H:15]2[S:14][C@H:13]([C:11]3[O:12][C:8]([Cl:7])=[CH:9][CH:10]=3)[C:18]3=[C:19]4[N:31]([CH3:32])[C:30](=[O:33])[N:29]([CH3:34])[C:28](=[O:35])[C:20]4=[C:21]([C:22]4[S:23][CH:24]=[C:25]([CH3:27])[N:26]=4)[N:17]3[CH2:16]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 4605971Sodium ImidazoleHCID 77106838HCID 77106838, compound

Product 1

HCID 90224123HCID 90224123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium imidazolide (86 mg, 0.960 mmol) was added to a solution of racemic 10-(5-chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazine-2,4(3H,10H)-dione (115 mg, 0.240 mmol) (Example 17) in DCM (24 ml) at 0° C. The mixture was stirred for 30 minutes, then trifluoromethanesulfonic anhydride (0.049 ml, 0.288 mmol) was added dropwise. The mixture was warmed to room temperature and stirred for 3 hours. The mixture was diluted with DCM (10 ml) washed with water (30 ml) and brine (30 ml). The organic layer was passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-20% methanol/DCM, afford the title compound as a mixture of diastereomers.

Workup

  1. stirringstirred for 3 hours
  2. washwashed with water (30 ml) and brine (30 ml)
  3. customevaporated under vacuum
  4. customPurification by chromatography on silica
  5. washeluting with 0-20% methanol/DCM

Sources & evidence

ORD record
ord-554032cf2fca4d6a9a4da753fe1261bb
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

Loading…