Trifluoroacetic acid → 3-(1H-benzo[d]imidazol-2-yl)-5-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

HRID 1959407Notes

Reaction equation

HRID 1959407 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:27]2[N:31](C(OC(C)(C)C)=O)[C:30]3[CH:39]=[CH:40][CH:41]=[CH:42][C:29]=3[N:28]=2)=[N:11][C:12]([C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH:20]=2)=[CH:13][N:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:28]1[C:29]2[CH:42]=[CH:41][CH:40]=[CH:39][C:30]=2[N:31]=[C:27]1[C:10]1[C:9]([NH2:8])=[N:14][CH:13]=[C:12]([C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:19][CH:20]=2)[N:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66745113Tert-butyl 2-(3-(bis(tert-butoxycarbonyl)amino)-6-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-yl)-1H-benzo[d]imidazole-1-carboxylate

Product 1

HCID 667455743-(1H-benzo[d]imidazol-2-yl)-5-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amineYield 14.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-(3-(bis(tert-butoxycarbonyl)amino)-6-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-yl)-1H-benzo[d]imidazole-1-carboxylate (100 mg, 0.1495 mmol) in DCM (1 mL) was treated with TFA (1 mL, 12.98 mmol) and allowed to stir at ambient temperature for 40 minutes. The reaction was concentrated in vacuo and 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, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a pale brown solid (8.0 mg, 14% Yield). 1H NMR (400.0 MHz, DMSO) d 2.84 (2H, m), 3.53 (2H, m), 3.94 (2H, m), 6.76-6.90 (3H, m), 7.20-7.69 (6H, m), 7.70-9.39 (4H, m), 12.88 (1H, m) ppm; MS (ES+) 369.02

Workup

  1. concentrationThe reaction was concentrated 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-9acc32b305194e87b1a50b2148df2df4
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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