Trifluoroacetic acid → HCID 59472012, compound

HRID 78664Notes

Reaction equation

HRID 78664 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]1[C:10]([C:27]2[O:31][C:30]([CH2:32][C:33]([O:35]C(C)(C)C)=[O:34])=[N:29][N:28]=2)=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:13][N:14]=1>C(Cl)Cl>[NH2:8][C:9]1[C:10]([C:27]2[O:31][C:30]([CH2:32][C:33]([OH:35])=[O:34])=[N:29][N:28]=2)=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59471678HCID 59471678, compound

Product 1

HCID 59472012HCID 59472012, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (500 μL, 6.490 mmol) was added to a stirred solution of tert-butyl 2-(5-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)acetate (45 mg, 0.083 mmol) in CH2Cl2 (5 mL) and the reaction stirred at ambient temperature for 18 h. The solvent was removed in vacuo and the residue azeotroped with CH2Cl2 (2×5 mL) and ether (2×5 mL). The material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3 CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound as a yellow solid (16.7 mg, 49%); 1H NMR (400 MHz, DMSO) d 1.19 (d, 6H), 3.45 (m, 1H), 4.27 (s, 2H), 7.85 (br s, 2H), 7.96 (d, 2H), 8.30 (d, 2H), 9.04 (s, 1H) and 13.30 (s, 1H) ppm; MS (ES+) 404.2

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with CH2Cl2 (2×5 mL) and ether (2×5 mL)
  3. customThe material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3 CN) over 16 minutes at 25 mL/min]
  4. customThe fractions were collected
  5. customfreeze-dried

Sources & evidence

ORD record
ord-a7ff1e080f2148ec8eced85f4c088673
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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