Trifluoroacetic acid → HCID 67086992, compound

HRID 2174998Notes

Reaction equation

HRID 2174998 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH:15]3[CH:10]([CH2:11][CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14]3)[CH2:9]2)=[O:7])=[C:4]([N:25]2[CH:29]=[CH:28][N:27]=[N:26]2)[N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C@H:15]12[N:8]([C:6]([C:5]3[C:4]([N:25]4[CH:29]=[CH:28][N:27]=[N:26]4)=[N:3][C:2]([CH3:1])=[CH:24][CH:23]=3)=[O:7])[CH2:9][C@H:10]1[CH2:11][CH2:12][NH:13][CH2:14]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67086585HCID 67086585, compound

Product 1

HCID 67086992HCID 67086992, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1S,6R)-tert-butyl 8-(6-methyl-2-(1H-1,2,3-triazol-1-yl)nicotinoyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate (1.05 g, 2.64 mmol) in DCM (15 mL) was added TFA (3 mL). The resulting mixture was allowed to stir at ambient temperature. After 16 h the mixture was concentrated under reduced pressure and the crude residue was purified by FCC (SiO2, gradient DCM to 15% MeOH/10% NH3/DCM) to yield the title compound (790 mg, 71%). MS (ESI) mass calcd. for C15H18N6O, 298.2; m/z found, 299.1 [M+H]+.

Workup

  1. concentrationAfter 16 h the mixture was concentrated under reduced pressure
  2. customthe crude residue was purified by FCC (SiO2, gradient DCM to 15% MeOH/10% NH3/DCM)

Sources & evidence

ORD record
ord-a6b02b4712f344af841d8339651f9556
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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