Trifluoroacetic acid → HCID 118045869, compound

HRID 595859Notes

Reaction equation

HRID 595859 reaction equation
[NH2:1][C:2]1[C:3]([C:22]2[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:24]([F:38])[CH:23]=2)=[N:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([O:14][Si](C(C)(C)C)(C)C)[CH2:9]2)=[CH:6][N:7]=1.C(=O)(O)[O-].[Na+].C(O)(C(F)(F)F)=O>Cl.C1COCC1.CO>[NH2:1][C:2]1[C:3]([C:22]2[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:24]([F:38])[CH:23]=2)=[N:4][C:5]([C@@H:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([OH:14])[CH2:9]2)=[CH:6][N:7]=1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 131734597HCID 131734597, compound

Product 1

HCID 118045869HCID 118045869, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(3-amino-6-(3-((tert-butyldimethylsilyl)oxy)cyclohexyl)pyrazin-2-yl)-N-benzyl-2-fluorobenzamide (61 mg, 0.114 mmol) in 6N HCl (0.29 mL),THF (0. 57 mL) and MeOH (0.285 mL) was stirred for 2 h. Solid sodium bicarbonate was added to neutralize the reaction mixture. Solvent was evaporated and 25% of the residue was dissolved in DMSO, and purified with auto-prep to provide 15 mg of desired cis racemate compound as a TFA salt. LCMS (m/z): 421.3 (MH+), 0.74 min. 1H NMR (400 MHz, MeOD-d4) δ ppm 7.82-7.69 (m, 2H) 7. 62-7. 45 (m, 2H) 7.37-7.12 (m, 5H) 4.52 (s, 2H) 3.66-3.52 (m, 1H) 2.75-2.60 (m, 1H) 2.11-2.01 (m, 1H) 1.97-1.70 (m, 3H) 1.52-1.29 (m, 3H) 1.24-1.08 (m, 1H).

Workup

  1. customSolvent was evaporated
  2. dissolution25% of the residue was dissolved in DMSO
  3. custompurified with auto-prep
  4. customto provide 15 mg
  5. custom421.3 (MH+), 0.74 min

Sources & evidence

ORD record
ord-d6f5c15d88c64cd698b2e92f3a597a35
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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