Nitrogen → HCID 58278823, compound

HRID 85106Notes

Reaction equation

HRID 85106 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([NH2:18])[C:11]=3[N:10]=2)[CH:6]=[CH:7][CH:8]=1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[N:24][CH:23]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].N#N.C([O-])(O)=O.[Na+]>ClCCCl>[N:24]1[CH:25]=[CH:26][CH:27]=[C:22]([CH2:21][NH:18][C:17]2[C:11]3[N:10]=[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:19])[F:20])[CH:4]=4)[NH:13][C:12]=3[CH:14]=[CH:15][CH:16]=2)[CH:23]=1

Participants

7

Reactant 5

HCID 947NitrogenHCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 636906712-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-amine

Product 1

HCID 58278823HCID 58278823, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture containing 2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-amine (13; 120 mg, 0.43 mmol), nicotinaldehyde (16; 51 mg, 0.47 mmol) and NaBH(OAc)3 (143 mg, 0.67 mmol) in 1,2-dichloroethane (10 mL) was stirred at room temperature for 12 h under an inert atmosphere of N2. Saturated aqueous NaHCO3 (10 mL) was added and the mixture was extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (gradient elution, petroleum ether:ethyl acetate=1:1 to 1:3) to afford N-(pyridin-3-ylmethyl)-2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-4-amine (Compound) (70 mg, 0.198 mmol, 46%) as a pale yellow solid. MS (ESI) calcd for C20H15F3N4: 368.12; found: 369 [M+H].

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×15 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography (gradient elution, petroleum ether:ethyl acetate=1:1 to 1:3)

Sources & evidence

ORD record
ord-d4607e09502946c3bba888f0c7c5e0a4
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

Loading…