4-[(2S)Oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-one → 4-[3-(2-{4-[2-(2-Cyclopentyl-ethyl)-imidazo[4,5-b]pyridin-3-yl]-phenyl}-ethylamino)-2-hydroxy-propoxy]-1,3-dihydro-benzoimidazol-2-one

HRID 1862779Notes

Reaction equation

HRID 1862779 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8]2[N:16]([C:17]3[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][NH2:23])=[CH:19][CH:18]=3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:26]1[CH2:28][C@H:27]1[CH2:29][O:30][C:31]1[C:39]2[NH:38][C:37](=[O:40])[NH:36][C:35]=2[CH:34]=[CH:33][CH:32]=1>C(Cl)(Cl)Cl.CO>[CH:1]1([CH2:6][CH2:7][C:8]2[N:16]([C:17]3[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][NH:23][CH2:28][CH:27]([OH:26])[CH2:29][O:30][C:31]4[C:39]5[NH:38][C:37](=[O:40])[NH:36][C:35]=5[CH:34]=[CH:33][CH:32]=4)=[CH:19][CH:18]=3)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 105124504-[(2S)Oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-oneHCID 18619611HCID 18619611, compound

Product 1

HCID 99152684-[3-(2-{4-[2-(2-Cyclopentyl-ethyl)-imidazo[4,5-b]pyridin-3-yl]-phenyl}-ethylamino)-2-hydroxy-propoxy]-1,3-dihydro-benzoimidazol-2-oneYield 8.7%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[2-(2-Cyclopentylethyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenethylamine (0.229 g, 0.68 mmol) was reacted with 4-[(2S)oxiranylmethoxy]-1,3-dihydro-2H-benzimidazol-2-one (0.141 g, 0.68 mmol) according to Procedure G (eluant: 20:1 going to 5:1 chloroform-methanol containing 1% ammonium hydroxide) to give the title compound (0.032 g, 0.059 mmol).

Sources & evidence

ORD record
ord-6a9c67c25ad8403b9303b8b4e36747df
Source dataset
uspto-grants-2003_03
Patent number
US06537994B2

Reaction notes

Loading…