3-Fluoro-4-(2-piperidin-1-ylethoxy)benzoyl chloride hydrochloride → Ethyl[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl][2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenyl]amine
Reaction equation
COC1C=C2C(=CC=1)CC(C1C(C)=CC=CC=1N)CC2.Cl.[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:26](Cl)=O.FC1C=[C:44](C=CC=1OCCN1CCCCC1)[CH2:45][NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([CH3:53])[C:48]=1[CH:54]1[CH2:63][CH2:62][C:61]2[C:56](=[CH:57][CH:58]=[C:59]([O:64][CH3:65])[CH:60]=2)[CH2:55]1>>[CH2:45]([N:46]([CH2:26][C:25]1[CH:29]=[CH:30][C:31]([O:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[C:23]([F:22])[CH:24]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([CH3:53])[C:48]=1[CH:54]1[CH2:63][CH2:62][C:61]2[C:56](=[CH:57][CH:58]=[C:59]([O:64][CH3:65])[CH:60]=2)[CH2:55]1)[CH3:44]Participants
4
Reactant 3
Product 1
Procedure
Synthesized from 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenylamine and 3-fluoro-4-(2-piperidin-1-ylethoxy)benzoyl chloride hydrochloride according to an analogous synthetic method to Example 152, [3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl][2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenyl]amine (578 mg) was used according to an analogous synthetic method to Example 36 to provide ethyl[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl][2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3-methylphenyl]amine (449 mg). This compound (447 mg) was used according to an analogous synthetic method to Example 111 to provide the title compound (317 mg).
Sources & evidence
- ORD record
- ord-94882b99ac334c7c9f724e646b5bed8d
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399520B2
Reaction notes
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