3-Fluoro-4-(2-piperidin-1-ylethoxy)benzoyl chloride hydrochloride → {2-[6-(Tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}ethyl[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amine

HRID 2423744Notes

Reaction equation

HRID 2423744 reaction equation
[Si](OC1C=C2C(=CC=1)CC(C1C=CC(OC)=CC=1N)CC2)(C(C)(C)C)(C)C.Cl.[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][C:38]=1[O:39][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[C:33](Cl)=O.[Si:48]([O:55][C:56]1[CH:57]=[C:58]2[C:63](=[CH:64][CH:65]=1)[CH2:62][CH:61]([C:66]1[CH:71]=[CH:70][C:69]([O:72][CH3:73])=[CH:68][C:67]=1[NH:74][CH2:75][C:76]1C=CC(OCCN3CCCCC3)=C(F)C=1)[CH2:60][CH2:59]2)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49]>>[Si:48]([O:55][C:56]1[CH:57]=[C:58]2[C:63](=[CH:64][CH:65]=1)[CH2:62][CH:61]([C:66]1[CH:71]=[CH:70][C:69]([O:72][CH3:73])=[CH:68][C:67]=1[N:74]([CH2:75][CH3:76])[CH2:33][C:32]1[CH:36]=[CH:37][C:38]([O:39][CH2:40][CH2:41][N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[C:30]([F:29])[CH:31]=1)[CH2:60][CH2:59]2)([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49]

Participants

4

Reactant 3

HCID 230871263-Fluoro-4-(2-piperidin-1-ylethoxy)benzoyl chloride hydrochlorideHCID 579340442-[6-(tert-Butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenylamineHCID 66626407{2-[6-(Tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amine

Product 1

HCID 66626257{2-[6-(Tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}ethyl[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amine

Procedure

Synthesized from 2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenylamine and 3-fluoro-4-(2-piperidin-1-ylethoxy)benzoyl chloride hydrochloride according to an analogous synthetic method to Example 152, {2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amine (480 mg) was used according to an analogous synthetic method to Example 36 to provide {2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}ethyl[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amine (405 mg). This compound (403 mg) was used according to an analogous synthetic method to Example 325 described below to provide the title compound (293 mg).

Sources & evidence

ORD record
ord-23513dc63d9248c08357e949e09fe697
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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