Ammonia → HCID 178424485, compound

HRID 2247158Notes

Reaction equation

HRID 2247158 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9](O)[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=4[N:17]=3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].N>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH3:8])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=3[N:17]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178425672HCID 178425672, compound

Product 1

HCID 178424485HCID 178424485, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared as described in Example 35 from 2-{4-[(3,4-dimethyl-phenyl)-hydroxy-methyl]-phenyl}-1H-benzoimidazole-5-carboxylic acid amide (Example 27, 14 mg, 0.03 mmol). Purification by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2) afforded 11.1 mg (83%) of the title, compound. TLC (silica, 1% methanol saturated with ammonia/9% methanol/CH2Cl2): Rf=0.39. HPLC (Method A): Rt=8.11. MS (ESI+): mass calculated for C23H21N3O, 855.2; m/z found, 356.1 [M+H]+. 1H NMR (500 MHz, CD3OD): δ 8.17 (s, 1H), 8.04 (d, J=8.2 Hz, 2H), 7.81 (br d, J=8.2 Hz, 1H), 7.63 (br s, 1H), 7.40 (d, J=8.2 Hz, 2H), 7.05 (d, J=7.71 Hz, 1H), 7.02 (s, 1H), 6.96 (d, J=7.6 Hz, 1H), 3.97 (s, 2H), 2.22 (d, J=4.1 Hz, 6H).

Workup

  1. customPurification by chromatography (silica gel, 1% methanol saturated with ammonia/9% methanol/CH2Cl2)
  2. customafforded 11.1 mg (83%) of the title, compound

Sources & evidence

ORD record
ord-8da3b60ee4244fd0aeb11efe7e6291a0
Source dataset
uspto-grants-2010_03
Patent number
US07687639B2

Reaction notes

Loading…