Trifluoroacetic acid → 5-[3-[(2S)-1-(Difluoromethoxy)propan-2-yl]oxy-5-(1H-pyrazol-3-ylcarbamoyl) phenoxy]-N,N-dimethyl-pyrazine-2-carboxamide

HRID 2241943Notes

Reaction equation

HRID 2241943 reaction equation
FC(F)(F)C(O)=O.[F:8][CH:9]([F:48])[O:10][CH2:11][C@@H:12]([O:14][C:15]1[CH:16]=[C:17]([CH:33]=[C:34]([O:36][C:37]2[CH:42]=[N:41][C:40]([C:43](=[O:47])[N:44]([CH3:46])[CH3:45])=[CH:39][N:38]=2)[CH:35]=1)[C:18]([NH:20][C:21]1[CH:25]=[CH:24][N:23](C(OC(C)(C)C)=O)[N:22]=1)=[O:19])[CH3:13]>C(Cl)Cl>[F:48][CH:9]([F:8])[O:10][CH2:11][C@@H:12]([O:14][C:15]1[CH:35]=[C:34]([CH:33]=[C:17]([C:18](=[O:19])[NH:20][C:21]2[CH:25]=[CH:24][NH:23][N:22]=2)[CH:16]=1)[O:36][C:37]1[N:38]=[CH:39][C:40]([C:43]([N:44]([CH3:46])[CH3:45])=[O:47])=[N:41][CH:42]=1)[CH3:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59205106HCID 59205106, compound

Product 1

HCID 1784617895-[3-[(2S)-1-(Difluoromethoxy)propan-2-yl]oxy-5-(1H-pyrazol-3-ylcarbamoyl) phenoxy]-N,N-dimethyl-pyrazine-2-carboxamideYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of tert-butyl 3-[[3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-benzoyl]amino]pyrazole-1-carboxylate (150 mg, 0.26 mmol) in DCM (16 mL) and stirred at RT for 2 hours. The solvent was removed in vacuo, DCM (20 mL) added and the mixture washed with water (20 mL), saturated sodium bicarbonate solution (20 mL), brine (20 mL), dried (MgSO4) and reduced in vacuo to give the desired compound (94 mg).

Workup

  1. customThe solvent was removed in vacuo, DCM (20 mL)
  2. additionadded
  3. washthe mixture washed with water (20 mL), saturated sodium bicarbonate solution (20 mL), brine (20 mL)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-0b1c261ed28a44b5bba35f11e3f873f3
Source dataset
uspto-grants-2010_03
Patent number
US07671060B2

Reaction notes

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