5-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine → [6-(2-Azepan-1-ylethoxy)pyridin-3-ylmethyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamine

HRID 1950158Notes

Reaction equation

HRID 1950158 reaction equation
Cl.[N:2]1([CH2:9][CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=O)=[CH:14][N:13]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.COC1C=CC(C2CCC3C(=CC=C(OC)C=3)C2)=[C:27]([NH2:29])C=1.N1(CCOC2N=CC(CN[C:60]3[CH:65]=[C:64]([O:66][CH3:67])[CH:63]=[CH:62][C:61]=3[CH:68]3[CH2:77][CH2:76][C:75]4[C:70](=[CH:71][CH:72]=[C:73]([O:78][CH3:79])[CH:74]=4)[CH2:69]3)=CC=2)CCCCCC1>>[N:2]1([CH2:9][CH2:10][O:11][C:12]2[N:13]=[CH:14][C:15]([CH2:16][NH:29][CH2:27][C:60]3[CH:65]=[C:64]([O:66][CH3:67])[CH:63]=[CH:62][C:61]=3[CH:68]3[CH2:69][CH2:70][C:71]4[C:76](=[CH:75][CH:74]=[C:73]([O:78][CH3:79])[CH:72]=4)[CH2:77]3)=[CH:19][CH:20]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 230872055-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineHCID 66626251[6-(2-Azepan-1-ylethoxy)pyridin-3-ylmethyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amineHCID 666267216-(2-Azepan-1-ylethoxy)nicotinic acid hydrochloride

Product 1

HCID 66627011[6-(2-Azepan-1-ylethoxy)pyridin-3-ylmethyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamine

Procedure

Synthesized from 6-(2-azepan-1-ylethoxy)nicotinic acid hydrochloride and 5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine according to an analogous synthetic method to Example 337 described below, [6-(2-azepan-1-ylethoxy)pyridin-3-ylmethyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (274 mg) was used according to an analogous synthetic method to Preparation Example 18 to provide [6-(2-azepan-1-ylethoxy)pyridin-3-ylmethyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamine (264 mg). This compound (262 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (122 mg).

Workup

  1. customwas used according to an analogous synthetic method to Preparation Example 18

Sources & evidence

ORD record
ord-c4793a158ffc46aa9c9365d7b68fceda
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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