Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate → HCID 178438622, compound

HRID 2048504Notes

Reaction equation

HRID 2048504 reaction equation
[CH3:1][C:2]([OH:18])([CH3:17])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[N:16]=[CH:15][NH:14][N:13]=2)[CH2:7][CH2:6]1.[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH:34]([C:40](=O)[CH2:41][CH2:42][CH3:43])[C:35](OCC)=[O:36])=[CH:29][CH:28]=1)#[N:20]>ClC1C=CC(Cl)=CC=1Cl>[OH:18][C:2]([CH3:1])([CH3:17])[CH2:3][O:4][C@@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]2[C:35](=[O:36])[C:34]([CH2:33][C:30]3[CH:31]=[CH:32][C:27]([C:22]4[C:21]([C:19]#[N:20])=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:28][CH:29]=3)=[C:40]([CH2:41][CH2:42][CH3:43])[N:13]3[N:14]=[CH:15][N:16]=[C:12]23)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178459389HCID 178459389, compound

Product 1

HCID 178438622HCID 178438622, compound

Reagents, catalysts & solvents 1

HCID 131,2,4-TrichlorobenzeneSolvent

Procedure

A solution of 2-methyl-1-{[4-(1H-1,2,4-triazol-3-ylamino)cyclohexyl]oxy}propan-2-ol (2.80 g) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (7.69 g) in 1,2,4-trichlorobenzene (15 mL) was stirred at 195° C. for 2 days. The reaction mixture was cooled to room temperature, and purified by silica gel chromatography [eluent: hexane/ethyl acetate=70/30→50/50 (volume ratio)] to give the title compound as a brown amorphous compound (620 mg, 10%).

Workup

  1. custompurified by silica gel chromatography [eluent: hexane/ethyl acetate=70/30→50/50 (volume ratio)]

Sources & evidence

ORD record
ord-c253b7b8b9d544cb9cbda54dc98fe9e9
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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