6-(2-(Ethylamino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl pivalate → 6-{2-{[4-(1-Azabicyclo[2.2.2]oct-4-ylmethoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 2423756Notes

Reaction equation

HRID 2423756 reaction equation
C(NC1C=C(OC)C=CC=1C1CCC2C=C(OC(=O)C(C)(C)C)C=CC=2C1)C.N12CCC(COC3C=CC(C=O)=CC=3)(CC1)CC2.[N:47]12[CH2:54][CH2:53][C:50]([CH2:55][O:56][C:57]3[CH:91]=[CH:90][C:60]([CH2:61][CH2:62][CH2:63][NH:64][C:65]4[CH:70]=[C:69]([O:71][CH3:72])[CH:68]=[CH:67][C:66]=4[CH:73]4[CH2:82][CH2:81][C:80]5[CH:79]=[C:78]([O:83]C(=O)C(C)(C)C)[CH:77]=[CH:76][C:75]=5[CH2:74]4)=[CH:59][CH:58]=3)([CH2:51][CH2:52]1)[CH2:49][CH2:48]2>>[N:47]12[CH2:54][CH2:53][C:50]([CH2:55][O:56][C:57]3[CH:58]=[CH:59][C:60]([CH2:61][CH2:62][CH2:63][NH:64][C:65]4[CH:70]=[C:69]([O:71][CH3:72])[CH:68]=[CH:67][C:66]=4[CH:73]4[CH2:82][CH2:81][C:80]5[CH:79]=[C:78]([OH:83])[CH:77]=[CH:76][C:75]=5[CH2:74]4)=[CH:90][CH:91]=3)([CH2:51][CH2:52]1)[CH2:49][CH2:48]2

Participants

4

Reactant 3

HCID 579340956-(2-(Ethylamino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl pivalateHCID 579343134-(1-Azabicyclo[2.2.2]oct-4-ylmethoxy)benzaldehydeHCID 66626957Pivalic acid 6-{2-{[4-(1-azabicyclo[2.2.2]oct-4-ylmethoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 666267656-{2-{[4-(1-Azabicyclo[2.2.2]oct-4-ylmethoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 69.6%

Procedure

Synthesized from pivalic acid 6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester and 4-(1-azabicyclo[2.2.2]oct-4-ylmethoxy)benzaldehyde according to an analogous synthetic method to Example 212, pivalic acid 6-{2-{[4-(1-azabicyclo[2.2.2]oct-4-ylmethoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) was used according to an analogous synthetic method to Example 217 to provide the title compound (18 mg).

Sources & evidence

ORD record
ord-00cfb147ab1b444cb4d414bd1d0be254
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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