Benzaldehyde → HCID 59349389, compound

HRID 415070Notes

Reaction equation

HRID 415070 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[NH:17][CH:16]=[N:15][C:14]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][CH3:35])[CH2:30][CH2:29]2)=[CH:23][C:22]=1[CH3:36])=[O:19])=[O:12].C(=O)[C:38]1[CH:43]=[CH:42]C=[CH:40][CH:39]=1.N1C2C=CC=CC=2N=C1NC(C1NC=NC=1C(NC1C=CC(OC2CCNCC2)=CC=1C)=O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>CN(C=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[NH:17][CH:16]=[N:15][C:14]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]3[CH:42]=[CH:43][CH:38]=[CH:39][CH:40]=3)[CH2:30][CH2:29]2)=[CH:23][C:22]=1[CH3:36])=[O:19])=[O:12]

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 24983964HCID 24983964, compoundHCID 59349428HCID 59349428, compound

Product 1

HCID 59349389HCID 59349389, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N5-1H-Benzimidazol-2-yl-N4-(2-methyl-4-{[1-(phenylmethyl)piperidin-4-yl]oxy}phenyl)-1H-imidazole-4,5-dicarboxamide was prepared in a similar manner as N5-1H-benzimidazol-2-yl-N4-{4-[(1-ethylpiperidin-4-yl)oxy]-2-methylphenyl}-1H-imidazole-4,5-dicarboxamide. Benzaldehyde and N5-(1H-benzo[d]imidazol-2-yl)-N4-(2-methyl-4-(piperidin-4-yloxy)phenyl)-1H-imidazole-4,5-dicarboxamide (0.1 mmol) were treated with a DMF solution of sodium triacetoxyborohydride. The reaction mixture was stir at room temperature over night (16 hours). The reaction mixture was then treated with 1 mL of 1N hydrochloric acid and concentrated under reduced pressure. The resulting crude material was purified by reverse phase HPLC (ammonium acetate/acetonitrile) to give 31 mg of N5-1H-benzimidazol-2-yl-N4-(2-methyl-4-{[1-(phenylmethyl)piperidin-4-yl]oxy}phenyl)-1H-imidazole-4,5-dicarboxamide as its acetate salt. 1H-NMR (400 MHz, DMSO-d6): 12.12 (s, 1H), 8.06 (s, 1H), 7.38 (m, 3H), 7.25 (m, 4H), 7.19 (m, 1H), 7.04 (m, 2H), 6.85 (d, 1H), 6.79 (dd, 1H), 4.34 (m, 1H), 3.43 (s, 2H), 2.60 (m, 2H), 2.44 (t, 2H), 2.18 (s, 3H), 1.88 (m, 2H), 1.58 (m, 2H); MS (EI): 550.9 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting crude material was purified by reverse phase HPLC (ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-7746ff0e48354638aae2af3e93535aff
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

Loading…