5-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine → [3-Fluoro-4-(3-piperidin-1-ylpropyl)phenyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

HRID 1950148Notes

Reaction equation

HRID 1950148 reaction equation
COC1C=CC(C2CCC3C(=CC=C(OC)C=3)C2)=C(N)C=1.BrC1C=CC(C#CCN2CCCCC2)=C(F)C=1.[F:39][C:40]1[CH:41]=[C:42]([NH:55][C:56]2[CH:61]=[C:60]([O:62][CH3:63])[CH:59]=[CH:58][C:57]=2[CH:64]2[CH2:73][CH2:72][C:71]3[C:66](=[CH:67][CH:68]=[C:69]([O:74][CH3:75])[CH:70]=3)[CH2:65]2)[CH:43]=[CH:44][C:45]=1[C:46]#[C:47][CH2:48][N:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1>>[F:39][C:40]1[CH:41]=[C:42]([NH:55][C:56]2[CH:61]=[C:60]([O:62][CH3:63])[CH:59]=[CH:58][C:57]=2[CH:64]2[CH2:73][CH2:72][C:71]3[C:66](=[CH:67][CH:68]=[C:69]([O:74][CH3:75])[CH:70]=3)[CH2:65]2)[CH:43]=[CH:44][C:45]=1[CH2:46][CH2:47][CH2:48][N:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1

Participants

4

Reactant 3

HCID 230872055-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineHCID 230875651-[3-(4-Bromo-2-fluorophenyl)prop-2-ynyl]piperidineHCID 66626185[3-Fluoro-4-(3-piperidin-1-ylprop-1-ynyl)phenyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

Product 1

HCID 66627362[3-Fluoro-4-(3-piperidin-1-ylpropyl)phenyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amineYield 83%

Procedure

Synthesized from 5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine and 1-[3-(4-bromo-2-fluorophenyl)prop-2-ynyl]piperidine according to an analogous synthetic method to Example 116, [3-fluoro-4-(3-piperidin-1-ylprop-1-ynyl)phenyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (281 mg) was used according to an analogous synthetic method to Example 22 to provide [3-fluoro-4-(3-piperidin-1-ylpropyl)phenyl][5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (235 mg). This compound (233 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (122 mg).

Sources & evidence

ORD record
ord-334c0e4119b44987b8acf94c1c92f6a2
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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