Trifluoroacetic acid → 3-(1-(4-aminophenyl)-1H-1,2,3-triazol-4-yl)-5-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-amine

HRID 1959387Notes

Reaction equation

HRID 1959387 reaction equation
C(OC([N:8]([C:16]1[C:21]([C:22]2[N:23]=[N:24][N:25]([C:27]3[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=3)[CH:26]=2)=[N:20][C:19]([N:34]2[CH2:39][CH2:38][N:37]([S:40]([CH2:43][CH3:44])(=[O:42])=[O:41])[CH2:36][CH2:35]2)=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:33][C:30]1[CH:29]=[CH:28][C:27]([N:25]2[CH:26]=[C:22]([C:21]3[C:16]([NH2:8])=[N:17][CH:18]=[C:19]([N:34]4[CH2:39][CH2:38][N:37]([S:40]([CH2:43][CH3:44])(=[O:42])=[O:41])[CH2:36][CH2:35]4)[N:20]=3)[N:23]=[N:24]2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66745858HCID 66745858, compound

Product 1

HCID 667450253-(1-(4-aminophenyl)-1H-1,2,3-triazol-4-yl)-5-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-amineYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl N-tert-butoxycarbonyl-3-(1-(4-aminophenyl)-1H-1,2,3-triazol-4-yl)-5-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-ylcarbamate (64 mg, 0.1016 mmol) was dissolved in DCM (5 mL) and treated with TFA (500 μL, 6.490 mmol). The reaction was allowed to stir at ambient temperature overnight and then the solvent removed in vacuo. The resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (24.3 mg, 30% Yield). 1H NMR (400.0 MHz, DMSO) d 1.24 (t, J=7.4 Hz, 3H), 3.11 (q, J=7.4 Hz, 2H), 3.30-3.33 (m, 4H), 3.50-3.52 (m, 4H), 6.77 (d, J=8.6 Hz, 2H), 7.67 (d, J=8.8 Hz, 2H), 7.88 (s, 1H) and 9.09 (s, 1H) ppm; MS (ES+) 430.0

Workup

  1. customthe solvent removed in vacuo
  2. customThe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were collected
  4. customfreeze-dried

Sources & evidence

ORD record
ord-6a844715530a448192908982c0bbdc9e
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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