Trifluoroacetic acid → HCID 118341213, compound

HRID 1753042Notes

Reaction equation

HRID 1753042 reaction equation
[CH:1]([N:4]1[C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[C:6]([C:13]([C:15]2[CH:16]=[C:17]([N:23](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:18]([O:21][CH3:22])=[N:19][CH:20]=2)=[O:14])=[CH:5]1)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:23][C:17]1[CH:16]=[C:15]([C:13]([C:6]2[C:7]3[CH:8]=[N:9][CH:10]=[CH:11][C:12]=3[N:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)=[O:14])[CH:20]=[N:19][C:18]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 118344727HCID 118344727, compound

Product 1

HCID 118341213HCID 118341213, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of di-tert-butyl {5-[(1-isopropyl-1H-pyrrolo[3,2-c]pyridin-3-yl)carbonyl]-2-methoxypyridin-3-yl}imidodicarbonate (Preparation 32, 250 mg, 0.5 mmol) in DCM (2.5 mL) at 0° C. was added TFA (0.75 mL) dropwise and the reaction stirred warming to room temperature for 5 hours. The reaction was basified by the addition of saturated aqueous NaHCO3 solution and extracted into DCM (3×30 mL). The organic layers were combined, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 5% MeOH in DCM to afford the title compound.

Workup

  1. extractionextracted into DCM (3×30 mL)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-6c628469d8f84d79a1eee3ae66097ace
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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