2-[6-(tert-Butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenylamine → [4-(2-Azepan-1-ylethoxy)benzyl]{2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}ethylamine

HRID 2423745Notes

Reaction equation

HRID 2423745 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][CH:14]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1N)[CH2:13][CH2:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.N1(CCOC2C=CC(C(Cl)=O)=CC=2)CCCCCC1.[N:48]1([CH2:55][CH2:56][O:57][C:58]2[CH:91]=[CH:90][C:61]([CH2:62][NH:63][C:64]3C=C(OC)C=C[C:65]=3C3CCC4C(=CC=C(O[Si](C(C)(C)C)(C)C)C=4)C3)=[CH:60][CH:59]=2)[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1>>[N:48]1([CH2:55][CH2:56][O:57][C:58]2[CH:59]=[CH:60][C:61]([CH2:62][NH:63][CH2:64][CH2:65][C:20]3[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:19]=3[CH:14]3[CH2:13][CH2:12][C:11]4[C:16](=[CH:17][CH:18]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH:10]=4)[CH2:15]3)=[CH:90][CH:91]=2)[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]1

Participants

4

Reactant 3

HCID 579340442-[6-(tert-Butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenylamineHCID 66627022[4-(2-Azepan-1-ylethoxy)benzyl]{2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}amineHCID 866052404-(2-Azepan-1-ylethoxy)benzoyl chloride hydrochloride

Product 1

HCID 66627675[4-(2-Azepan-1-ylethoxy)benzyl]{2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}ethylamine

Procedure

Synthesized from 2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenylamine and 4-(2-azepan-1-ylethoxy)benzoyl chloride hydrochloride according to an analogous synthetic method to Example 152, [4-(2-azepan-1-ylethoxy)benzyl]{2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}amine (448 mg) was used according to an analogous synthetic method to Example 36 to provide [4-(2-azepan-1-ylethoxy)benzyl]{2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}ethylamine (392 mg). This compound (390 mg) was used according to an analogous synthetic method to Example 325 described below to provide the title compound (254 mg).

Sources & evidence

ORD record
ord-7896a5dc058b495d898d847bbe585940
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

Loading…