HCID 59784811, compound → HCID 67058658, compound

HRID 470330Notes

Reaction equation

HRID 470330 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][N:4]([C:10]2[N:19]=[CH:18][C:17]3[CH2:16][CH2:15][C:14]4[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:13]=4[C:12]=3[N:11]=2)[N:3]=1.BrC1C=CC2[NH:31]C(C(Cl)(Cl)Cl)=NC=2C=1>CC(N(C)C)=O>[NH2:1][C:2]1[C:6]([C:7]([NH2:31])=[O:9])=[CH:5][N:4]([C:10]2[N:19]=[CH:18][C:17]3[CH2:16][CH2:15][C:14]4[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:13]=4[C:12]=3[N:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 59784811HCID 59784811, compoundHCID 178478477HCID 178478477, compound

Product 1

HCID 67058658HCID 67058658, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of benzimidazole-2-aldehyde 1 (0.5 mmol) and diamine 2 (0.5 mmol) in dimethylacetamide (4 mL) was stirred at 100° C. for 12 h. Solvent was evaporated and residue was purified by preparative HPLC to give benzimidazole derivative 3. 1H NMR (300 MHz, MeOH-d4): δ 2.52 (s, 3H), 2.85 (brs, 4H), 3.25 (brs, 4H), 7.05-7.15 (m, 2H), 7.25-7.35 (s overlapped with m, 2H), 7.60-7.75 (m, 4H); LCMS m/z 333 (M+H+), ELSD 99%.

Workup

  1. customSolvent was evaporated
  2. customresidue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c98c185a80ea457fa71d613308d87c57
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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