Isopropyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine → 6-{2-{[3-Fluoro-4-(2-piperidin-1-ylethoxy)benzyl]isopropylamino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 2423742Notes

Reaction equation

HRID 2423742 reaction equation
C(NC1C=C(OC)C=CC=1C1CCC2C(=CC=C(OC)C=2)C1)(C)C.Cl.FC1C=C(C=CC=1OCCN1CCCCC1)C(O)=O.[F:45][C:46]1[CH:47]=[C:48]([CH:74]=[CH:75][C:76]=1[O:77][CH2:78][CH2:79][N:80]1[CH2:85][CH2:84][CH2:83][CH2:82][CH2:81]1)[CH2:49][N:50]([CH:71]([CH3:73])[CH3:72])[C:51]1[CH:56]=[C:55]([O:57]C)[CH:54]=[CH:53][C:52]=1[CH:59]1[CH2:68][CH2:67][C:66]2[C:61](=[CH:62][CH:63]=[C:64]([O:69]C)[CH:65]=2)[CH2:60]1>>[F:45][C:46]1[CH:47]=[C:48]([CH:74]=[CH:75][C:76]=1[O:77][CH2:78][CH2:79][N:80]1[CH2:85][CH2:84][CH2:83][CH2:82][CH2:81]1)[CH2:49][N:50]([CH:71]([CH3:73])[CH3:72])[C:51]1[CH:56]=[C:55]([OH:57])[CH:54]=[CH:53][C:52]=1[CH:59]1[CH2:68][CH2:67][C:66]2[CH:65]=[C:64]([OH:69])[CH:63]=[CH:62][C:61]=2[CH2:60]1

Participants

4

Reactant 3

HCID 23087105Isopropyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amineHCID 666268273-Fluoro-4-(2-piperidin-1-ylethoxy)benzoic acid hydrochlorideHCID 66627004[3-Fluoro-4-(2-piperidin-1-ylethoxy)benzyl]isopropyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

Product 1

HCID 579342956-{2-{[3-Fluoro-4-(2-piperidin-1-ylethoxy)benzyl]isopropylamino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 68.6%

Procedure

Synthesized from isopropyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine and 3-fluoro-4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride according to an analogous synthetic method to Example 152, [3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]isopropyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (402 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (262 mg).

Sources & evidence

ORD record
ord-2afab17f29ec4cd99efcc712f8295197
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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