2-Methoxyethylamine → 2-[[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]amino]-N-(2-methoxyethyl)-acetamide

HRID 276000Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH:10][C@@H:11]([CH3:21])[C@H:12]([OH:20])[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:5]=[C:4]([Cl:22])[C:3]=1[NH:23][CH2:24][C:25](OCC)=[O:26].[CH3:30][O:31][CH2:32][CH2:33][NH2:34]>>[Cl:22][C:4]1[CH:5]=[C:6]([CH2:8][CH2:9][NH:10][C@@H:11]([CH3:21])[C@H:12]([OH:20])[C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)[CH:7]=[C:2]([Cl:1])[C:3]=1[NH:23][CH2:24][C:25]([NH:34][CH2:33][CH2:32][O:31][CH3:30])=[O:26]

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 10717980HCID 10717980, compound

Product 1

HCID 699893952-[[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]amino]-N-(2-methoxyethyl)-acetamide

Conditions

Temperature: 80 °C

Procedure

Ethyl N-[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]aminoacetate (44.3 mg) was dissolved in 2-methoxyethylamine (886 μl), and the solution was stirred for 48 hours at 80° C. The reaction mixture was concentrated in vacuo, and purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: dichloromethane/methanol=10/1) gave 2-[[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]amino]-N-(2-methoxyethyl)-acetamide (27.7 mg).

Workup

concentrationThe reaction mixture was concentrated in vacuo, and purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record: ord-a96e9fdfa4094711a14144ed860804ba
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353025B1

Reaction notes

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