4-Chlorobenzaldehyde → HCID 57639712, compound

HRID 2111794Notes

Reaction equation

HRID 2111794 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1>CO.CC(O)=O>[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:1][C:2]2[CH:3]=[C:4]([N:8]3[C:12]4[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[O:18])=[CH:16][C:11]=4[N:10]=[CH:9]3)[CH:5]=[CH:6][CH:7]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 69067477HCID 69067477, compound

Product 1

HCID 57639712HCID 57639712, compound

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

A mixture of 1-(3-aminophenyl)-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide (1.0 eq) and 4-chlorobenzaldehyde (1.0 eq) in MeOH:HOAc (10:1 v/v, 0.017M) was stirred for 15 min at rt prior to the addition of (polystyrylmethyl)trimethylammonium cyanoborohydride (3.5-5.0 mmol/g, 2.5 eq). The reaction mixture was shaken at rt overnight in a capped vial and then filtered through a plug of cotton wool. The resin was washed with MeOH and the combined filtrate and MeOH washings were concentrated under reduced pressure and purified by silica gel chromatography eluting with 5% MeOH in DCM to yield 1-{3-[(4-chlorobenzyl)amino]phenyl}-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide. 1H-NMR (CD3OD, 400 MHz): δ 4.38 (s, 2H), 4.89 (s, 2H), 6.68 (s, 1H), 6.76 (dd, J=2.0 Hz, 7.0 Hz, 2H), 7.20-7.45 (m, 7H), 7.81 (dd, J=8.4 Hz, 1.6 Hz, 1H), 7.89 (d, J=6.0 Hz, 1H), 8.26 (d, J=1.2 Hz, 1H), 8.42 (s, 1H), 8.45 (d, J=4 Hz, 1H), 8.60 (s, 1H). MS (ES+): m/z 469 [MH+]

Workup

  1. stirringThe reaction mixture was shaken at rt overnight in a capped vial and
  2. filtrationthen filtered through a plug of cotton wool
  3. washThe resin was washed with MeOH
  4. concentrationthe combined filtrate and MeOH washings were concentrated under reduced pressure
  5. custompurified by silica gel chromatography
  6. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-e3d4a7f1ac064af380d7dcf23b33c2df
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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