4-{2-{Cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}ethyl}phenol → 6-{2-{{2-[4-(2-Azepan-1-ylethoxy)phenyl]ethyl}cyclopropylmethylamino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950343Notes

Reaction equation

HRID 1950343 reaction equation
C1(CN(C2C=C(OC)C=CC=2C2CCC3C(=CC=C(OC)C=3)C2)CCC2C=CC(O)=CC=2)CC1.Cl.ClCCN1CCCCCC1.[N:46]1([CH2:53][CH2:54][O:55][C:56]2[CH:61]=[CH:60][C:59]([CH2:62][CH2:63][N:64]([CH2:85][CH:86]3[CH2:88][CH2:87]3)[C:65]3[CH:70]=[C:69]([O:71]C)[CH:68]=[CH:67][C:66]=3[CH:73]3[CH2:82][CH2:81][C:80]4[C:75](=[CH:76][CH:77]=[C:78]([O:83]C)[CH:79]=4)[CH2:74]3)=[CH:58][CH:57]=2)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>>[N:46]1([CH2:53][CH2:54][O:55][C:56]2[CH:61]=[CH:60][C:59]([CH2:62][CH2:63][N:64]([CH2:85][CH:86]3[CH2:87][CH2:88]3)[C:65]3[CH:70]=[C:69]([OH:71])[CH:68]=[CH:67][C:66]=3[CH:73]3[CH2:82][CH2:81][C:80]4[CH:79]=[C:78]([OH:83])[CH:77]=[CH:76][C:75]=4[CH2:74]3)=[CH:58][CH:57]=2)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

Participants

4

Reactant 3

HCID 230875484-{2-{Cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}ethyl}phenolHCID 24188283N-(2-chloroethyl)perhydroazepine hydrochlorideHCID 66626512{2-[4-(2-Azepan-1-ylethoxy)phenyl]ethyl}cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

Product 1

HCID 579340686-{2-{{2-[4-(2-Azepan-1-ylethoxy)phenyl]ethyl}cyclopropylmethylamino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 50.4%

Procedure

Synthesized from 4-{2-{cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}ethyl}phenol and 1-(2-chloroethyl)azepane hydrochloride according to an analogous synthetic method to Preparation Example 40, {2-[4-(2-azepan-1-ylethoxy)phenyl]ethyl}cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (392 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (188 mg).

Sources & evidence

ORD record
ord-312d85002947451bb23f71dbee7cc112
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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