2-Chloroethyldiisopropylammonium chloride → 6-{2-[5-(2-Diisopropylaminoethoxy)-1,3-dihydroisoindol-2-yl]-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950293Notes

Reaction equation

HRID 1950293 reaction equation
COC1C=CC(C2CCC3C(=CC=C(OC)C=3)C2)=C(N2CC3C(=CC=C(O)C=3)C2)C=1.Cl.ClCCN(C(C)C)C(C)C.[CH:42]([N:45]([CH:78]([CH3:80])[CH3:79])[CH2:46][CH2:47][O:48][C:49]1[CH:50]=[C:51]2[C:55](=[CH:56][CH:57]=1)[CH2:54][N:53]([C:58]1[CH:63]=[C:62]([O:64]C)[CH:61]=[CH:60][C:59]=1[CH:66]1[CH2:75][CH2:74][C:73]3[C:68](=[CH:69][CH:70]=[C:71]([O:76]C)[CH:72]=3)[CH2:67]1)[CH2:52]2)([CH3:44])[CH3:43]>>[CH:78]([N:45]([CH:42]([CH3:44])[CH3:43])[CH2:46][CH2:47][O:48][C:49]1[CH:50]=[C:51]2[C:55](=[CH:56][CH:57]=1)[CH2:54][N:53]([C:58]1[CH:63]=[C:62]([OH:64])[CH:61]=[CH:60][C:59]=1[CH:66]1[CH2:75][CH2:74][C:73]3[CH:72]=[C:71]([OH:76])[CH:70]=[CH:69][C:68]=3[CH2:67]1)[CH2:52]2)([CH3:79])[CH3:80]

Participants

4

Reactant 3

HCID 779422-Chloroethyldiisopropylammonium chlorideHCID 579338902-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindol-5-olHCID 66627050diisopropyl{2-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindol-5-yloxy}ethyl}amine

Product 1

HCID 579345606-{2-[5-(2-Diisopropylaminoethoxy)-1,3-dihydroisoindol-2-yl]-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 52%

Procedure

Synthesized from 2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindol-5-ol and (2-chloroethyl)diisopropylamine hydrochloride according to an analogous synthetic method to Preparation Example 40, diisopropyl {2-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2,3-dihydro-1H-isoindol-5-yloxy}ethyl}amine (126 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (62 mg).

Sources & evidence

ORD record
ord-18d881798c734502bf012b7dc97a48be
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

Loading…