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

HRID 1959409Notes

Reaction equation

HRID 1959409 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:28]2[N:32](C(OC(C)(C)C)=O)[C:31]3[CH:40]=[CH:41][CH:42]=[CH:43][C:30]=3[N:29]=2)=[N:11][C:12]([C:15]2[CH2:16][CH2:17][N:18](C(OC(C)(C)C)=O)[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:29]1[C:30]2[CH:43]=[CH:42][CH:41]=[CH:40][C:31]=2[N:32]=[C:28]1[C:10]1[C:9]([NH2:8])=[N:14][CH:13]=[C:12]([C:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH:20]=2)[N:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66745281tert-butyl 2-[3-(bis(tert-butoxycarbonyl)amino)-6-(1-tert-butoxycarbonyl-3,6-dihydro-2H-pyridin-4-yl)pyrazin-2-yl]benzimidazole-1-carboxylate

Product 1

HCID 667451703-(1H-benzo[d]imidazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amineYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-(3-(bis(tert-butoxycarbonyl)amino)-6-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-yl)-1H-benzo[d]imidazole-1-carboxylate (1.7248 g, 2.490 mmol) in DCM (17.25 mL) was treated with TFA (5 mL, 64.90 mmol) and left to stir at ambient temperature for 4 hours. The reaction mixture was concentrated in vacuo and triturated from MeOH/Toluene and the resultant orange solid was filtered off (622 mg, 48% Yield). 1H NMR (400.0 MHz, DMSO) d 2.90 (2H, m), 3.41 (2H, m), 3.96 (2H, m), 6.80 (1H, m), 7.09-7.30 (4H, m), 7.82 (2H, br s), 8.52 (1H, s) ppm; MS (ES+) 293.03

Workup

  1. waitleft
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customtriturated from MeOH/Toluene
  4. filtrationthe resultant orange solid was filtered off (622 mg, 48% Yield)

Sources & evidence

ORD record
ord-970d817ca8524bc9a26171fb69d2b280
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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