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

HRID 549646Notes

Reaction equation

HRID 549646 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[C:18]([O:20][CH2:21][CH:22]3[CH2:24][CH2:23]3)[CH:17]=[C:16](Br)[CH:15]=2)=[CH:9][C:8]=1[CH3:26])[CH3:2].[CH2:28]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[C:29]#[CH:30].C(OC(=O)COC1C=CC(SC2C=C(C#CC3C=CC(CO)=CC=3)C=C(OCCC3C=CC(Cl)=CC=3)C=2)=CC=1C)C>>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:15]=[C:16]([C:30]#[C:29][CH2:28][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:17]=[C:18]([O:20][CH2:21][CH:22]3[CH2:24][CH2:23]3)[CH:19]=2)=[CH:9][C:8]=1[CH3:26])[CH3:2]

Participants

4

Reactant 3

HCID 4129414-(2-Propyn-1-yl)morpholineHCID 58368330[4-(3-Bromo-5-cyclopropylmethoxy-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 67169962{4-[3-Cyclopropylmethoxy-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-cyclopropylmethoxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester (250 mg; 0.55 mmol) and 4-prop-2-ynyl-morpholine (208 mg; 1.7 mmol) applying the procedure described for {4-[3-[2-(4-Chlorophenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester. The crude product was purified by preparative HPLC (method B). Yield: 205 mg; 75%. HPLC-MS: m/z: 496.1 (M+H)+; Rt: 2.04 min.

Workup

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

Sources & evidence

ORD record
ord-7da48ec138d64df39e99fca54c8dc7d8
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Reaction notes

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