Methanol → HCID 178468683, compound
Reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:26]([O:28][C:29]([C:31]1[CH:47]=[CH:46][C:34]2[NH:35][C:36]([NH:38][CH2:39][CH:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)=[N:37][C:33]=2[CH:32]=1)=[O:30])[CH3:27].CO>CN(C)C=O.C(O)(=O)C>[CH2:26]([O:28][C:29]([C:31]1[CH:47]=[CH:46][C:34]2[NH:35][C:36]([NH:38][CH2:39][CH:40]3[CH2:41][CH2:42][N:43]([CH2:5][C:4]4[CH:7]=[C:8]([Cl:10])[CH:9]=[C:2]([Cl:1])[C:3]=4[OH:11])[CH2:44][CH2:45]3)=[N:37][C:33]=2[CH:32]=1)=[O:30])[CH3:27]Participants
Procedure
After adding 3,5-dichloro-2-hydroxybenzaldehyde (0.3 mmol) and sodium triacetoxyborohydride (0.3 mmol) to a solution of 2-[(piperidin-4-ylmethyl)-amino]-1H-benzimidazole-5-carboxylic acid ethyl ester (0.1 mmol) in dimethylformamide-acetic acid (10:1) (1.0 ml), the mixture was stirred at room temperature overnight. Methanol (1.0 ml) was added to the reaction mixture to suspend the reaction, and after stirring for 1 hour, the solution was passed through SCX (Bond Elute SCX500MG). The SCX was washed with methanol and then with a mixed solution of chloroform/methanol (1/1), and elution was performed with a 0.5N ammonia-dioxane solution. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to preparative HPLC to obtain 2-{[1-(3,5-dichloro-2-hydroxybenzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-5-carboxylic acid ethyl ester. The compound was identified by LC-MS.
Workup
- customthe reaction
- stirringafter stirring for 1 hour
- washthe solution was passed through SCX (Bond Elute SCX500MG)
- washThe SCX was washed with methanol
- washwith a mixed solution of chloroform/methanol (1/1), and elution
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-74089050066a497ab8d99866e42b433c
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517875B2
Reaction notes
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