Triethylamine → HCID 77107022, compound

HRID 2201234Notes

Reaction equation

HRID 2201234 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[Cl:16][C:17]1[N:18]=[C:19]([CH:22](O)[CH2:23][CH2:24][N:25]2[C:33]([C:34]3[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=3)[C:37]#[N:38])=[C:32]3[C:27]([N:28]([CH3:45])[C:29](=[O:44])[N:30]([CH3:43])[C:31]3=[O:42])=[CH:26]2)[S:20][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:16][C:17]1[N:18]=[C:19]([CH:22]2[C:26]3[N:25]([C:33]([C:34]4[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=4)[C:37]#[N:38])=[C:32]4[C:31](=[O:42])[N:30]([CH3:43])[C:29](=[O:44])[N:28]([CH3:45])[C:27]4=3)[CH2:24][CH2:23]2)[S:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 67749Trifluoromethanesulfonic anhydride2×HCID 86723467HCID 86723467, compound

Product 1

HCID 77107022HCID 77107022, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.445 mL, 2.63 mmol) was added to a solution of 3-(6-(3-(4-chlorothiazol-2-yl)-3-hydroxypropyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (600 mg, 1.316 mmol) and triethylamine (0.550 mL, 3.95 mmol) in DCM (20 mL). The mixture was stirred at room temperature for 90 mins. Further portions of triethylamine (0.550 mL, 3.95 mmol) and trifluoromethanesulfonic anhydride (0.445 mL, 2.63 mmol) were added to allow the reaction to run to completion. The reaction mixture was quenched with saturated NaHCO3(aq) and extracted with DCM (3×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-80% EtOAc/hexane gave a crude material which was triturated with DCM/diethyl ether/hexane to afford the title compound.

Workup

  1. customthe reaction
  2. customThe reaction mixture was quenched with saturated NaHCO3(aq)
  3. extractionextracted with DCM (3×)
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 20-80% EtOAc/hexane
  7. customgave a crude material which
  8. customwas triturated with DCM/diethyl ether/hexane

Sources & evidence

ORD record
ord-cfd396167983487fadb45ef24877ac44
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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