1-(2-Chloroethyl)pyrrolidine hydrochloride → 6-{2-{Cyclopropylmethyl {2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]ethyl}amino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950344Notes

Reaction equation

HRID 1950344 reaction equation
C1(CN(C2C=C(OC)C=CC=2C2CCC3C(=CC=C(OC)C=3)C2)CCC2C=CC(O)=CC=2)CC1.Cl.ClCCN1CCCC1.[CH:44]1([CH2:47][N:48]([C:65]2[CH:70]=[C:69]([O:71]C)[CH:68]=[CH:67][C:66]=2[CH:73]2[CH2:82][CH2:81][C:80]3[C:75](=[CH:76][CH:77]=[C:78]([O:83]C)[CH:79]=3)[CH2:74]2)[CH2:49][CH2:50][C:51]2[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH2:59][N:60]3[CH2:64][CH2:63][CH2:62][CH2:61]3)=[CH:53][CH:52]=2)[CH2:46][CH2:45]1>>[CH:44]1([CH2:47][N:48]([CH2:49][CH2:50][C:51]2[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH2:59][N:60]3[CH2:64][CH2:63][CH2:62][CH2:61]3)=[CH:53][CH:52]=2)[C:65]2[CH:70]=[C:69]([OH:71])[CH:68]=[CH:67][C:66]=2[CH:73]2[CH2:82][CH2:81][C:80]3[CH:79]=[C:78]([OH:83])[CH:77]=[CH:76][C:75]=3[CH2:74]2)[CH2:45][CH2:46]1

Participants

4

Reactant 3

HCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 230875484-{2-{Cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}ethyl}phenolHCID 66626515Cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]{2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]ethyl}amine

Product 1

HCID 579344076-{2-{Cyclopropylmethyl {2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]ethyl}amino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 89.4%

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)pyrrolidine hydrochloride according to an analogous synthetic method to Preparation Example 40, cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]{2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]ethyl}amine (284 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (241 mg).

Sources & evidence

ORD record
ord-89d7c9b3ff5c44ca8242028830d39fa3
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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