Acetic Acid → HCID 68505475, compound

HRID 1716564Notes

Reaction equation

C(OC([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[NH2:20])[CH:8]([O:21][CH3:22])[CH2:7]1)=O)C.C(OC(O[CH2:32][CH3:33])(OCC)C)C.[C:34](O)(=O)C>>[CH2:32]([C:33]1[N:12]([CH:9]2[CH2:10][CH2:11][NH:6][CH2:7][CH:8]2[O:21][CH3:22])[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[N:20]=1)[CH3:34]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 66221Triethyl orthoacetate

HCID 68509287HCID 68509287, compound

Product 1

HCID 68505475HCID 68505475, compound

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(2-amino-4-methyl-phenylamino)-3-methoxy-piperidine-1-carboxylic acid ethyl ester (800 mg, 2.60 mmol) in acetic acid (5 mL) was added 1,1,1-triethoxy ethane (550 mg, 3.12 mmol). After heating at 60° C. for 30 minutes, the mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (15/1 CH2Cl2/CH3OH) to 4-(2-ethyl-5-methyl-benzoimidazol-1-yl)-3-methoxy-piperidine-1-carboxylic acid ethyl ester (940 mg, 89%) as a white solid.

Workup

concentrationthe mixture was concentrated under reduced pressure
customthe residue was purified by flash chromatography (15/1 CH2Cl2/CH3OH) to 4-(2-ethyl-5-methyl-benzoimidazol-1-yl)-3-methoxy-piperidine-1-carboxylic acid ethyl ester (940 mg, 89%) as a white solid

Sources & evidence

ORD record: ord-8abdbe856902491ba2a1fa9c69a00d6e
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803816B2

Reaction notes

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