4-(2-Propyn-1-yl)morpholine → {4-[3-(2-Cyclohexyl-ethoxy)-5-(3-morpholin-4-yl-prop-1-ynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic Acid Ethyl Ester

HRID 1513178Notes

Reaction equation

HRID 1513178 reaction equation
C(OC(=O)COC1C=CC(SC2C=C(OCC3CCCC3)C=C(Br)C=2)=CC=1C)C.[CH2:30]([N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)[C:31]#[CH:32].[CH2:39]([O:41][C:42](=[O:79])[CH2:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([S:51][C:52]2[CH:57]=[C:56](C#CC3C=CC(CO)=CC=3)[CH:55]=[C:54]([O:68][CH2:69][CH2:70][C:71]3[CH:76]=[CH:75][C:74](Cl)=[CH:73][CH:72]=3)[CH:53]=2)=[CH:47][C:46]=1[CH3:78])[CH3:40]>>[CH2:39]([O:41][C:42](=[O:79])[CH2:43][O:44][C:45]1[CH:50]=[CH:49][C:48]([S:51][C:52]2[CH:57]=[C:56]([C:32]#[C:31][CH2:30][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH:55]=[C:54]([O:68][CH2:69][CH2:70][CH:71]3[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76]3)[CH:53]=2)=[CH:47][C:46]=1[CH3:78])[CH3:40]

Participants

4

Reactant 3

HCID 4129414-(2-Propyn-1-yl)morpholineHCID 57791902[4-(3-Bromo-5-cyclopentylmethoxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl EsterHCID 67024299{4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methylphenoxy}-acetic acid ethyl ester

Product 1

HCID 67171335{4-[3-(2-Cyclohexyl-ethoxy)-5-(3-morpholin-4-yl-prop-1-ynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic Acid Ethyl Ester

Procedure

The title product was prepared from {4-[3-Bromo-5-cyclopentylmethoxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester (260 mg; 0.54 mmol) and 4-prop-2-ynyl-morpholine (203.6 mg; 1.63 mmol) applying the procedure described for {4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester. The crude product was purified by preparative HPLC (method B). Yield: 80 mg (28%). HPLC-MS: m/z: 523.9 (M)+; Rt: 2.19 min

Workup

  1. customThe crude product was purified by preparative HPLC (method B)

Sources & evidence

ORD record
ord-0c51ad0cdaca419d96132c38694a8415
Source dataset
uspto-grants-2012_07
Patent number
US08217086B2

Reaction notes

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