1-[2-(4-Bromophenoxy)ethyl]azepane → 6-{2-[4-(2-Azepan-1-ylethoxy)phenylamino]-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950144Notes

Reaction equation

HRID 1950144 reaction equation
COC1C=CC(C2CCC3C(=CC=C(OC)C=3)C2)=C(N)C=1.BrC1C=CC(OCCN2CCCCCC2)=CC=1.[N:39]1([CH2:46][CH2:47][O:48][C:49]2[CH:54]=[CH:53][C:52]([NH:55][C:56]3[CH:61]=[C:60]([O:62]C)[CH:59]=[CH:58][C:57]=3[CH:64]3[CH2:73][CH2:72][C:71]4[C:66](=[CH:67][CH:68]=[C:69]([O:74]C)[CH:70]=4)[CH2:65]3)=[CH:51][CH:50]=2)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>>[N:39]1([CH2:46][CH2:47][O:48][C:49]2[CH:50]=[CH:51][C:52]([NH:55][C:56]3[CH:61]=[C:60]([OH:62])[CH:59]=[CH:58][C:57]=3[CH:64]3[CH2:73][CH2:72][C:71]4[CH:70]=[C:69]([OH:74])[CH:68]=[CH:67][C:66]=4[CH2:65]3)=[CH:53][CH:54]=2)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

4

Reactant 3

HCID 130635441-[2-(4-Bromophenoxy)ethyl]azepaneHCID 230872055-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineHCID 66626615[4-(2-Azepan-1-ylethoxy)phenyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

Product 1

HCID 579342656-{2-[4-(2-Azepan-1-ylethoxy)phenylamino]-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 34.5%

Procedure

Synthesized from 5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine and 1-[2-(4-bromophenoxy)ethyl]azepane according to an analogous synthetic method to Example 116, [4-(2-azepan-1-ylethoxy)phenyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (86 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (28 mg).

Sources & evidence

ORD record
ord-f2a2b961c6e74ab1b73a51128917f8b5
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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