N-{3-[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-phenyl}-acetamide → (3-Chloro-isoquinolin-1-yl)-[1-(2,6-diethoxy-4'-fluoro-biphenyl-4-ylmethyl)-piperidin-4-yl]-amine

HRID 2355616Notes

Reaction equation

HRID 2355616 reaction equation
ClC1C=CC(CN2CCC(NC3C=C(NC(=O)C)C=CC=3)CC2)=CC=1OCC.Cl.Cl.[Cl:31][C:32]1[N:33]=[C:34]([NH:42][CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2.[CH2:49]([O:51][C:52]1[CH:57]=[C:56]([CH:58]=O)[CH:55]=[C:54]([O:60][CH2:61][CH3:62])[C:53]=1[C:63]1[CH:68]=[CH:67][C:66]([F:69])=[CH:65][CH:64]=1)[CH3:50]>>[Cl:31][C:32]1[N:33]=[C:34]([NH:42][CH:43]2[CH2:48][CH2:47][N:46]([CH2:58][C:56]3[CH:55]=[C:54]([O:60][CH2:61][CH3:62])[C:53]([C:63]4[CH:68]=[CH:67][C:66]([F:69])=[CH:65][CH:64]=4)=[C:52]([O:51][CH2:49][CH3:50])[CH:57]=3)[CH2:45][CH2:44]2)[C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2

Participants

4

Reactant 3

HCID 24854968N-{3-[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-phenyl}-acetamideHCID 593831002,6-Diethoxy-4'-fluoro-biphenyl-4-carbaldehydeHCID 86618559(3-Chloro-isoquinolin-1-yl)-piperidin-4-yl-amine dihydrochloride

Product 1

HCID 86618560(3-Chloro-isoquinolin-1-yl)-[1-(2,6-diethoxy-4'-fluoro-biphenyl-4-ylmethyl)-piperidin-4-yl]-amine

Procedure

The title compound was prepared in analogy to the synthesis of 6-[1-(3-ethoxy-4-methyl-benzyl)-piperidin-4-ylamino]-nicotinonitrile (example 38/step 3) from (3-chloro-isoquinolin-1-yl)-piperidin-4-yl-amine dihydrochloride (intermediate B13) and 2,6-diethoxy-4′-fluoro-biphenyl-4-carbaldehyde (intermediate E22) in a yield of 8.9 mg (11%). MS (ISP): 534.5 [M+H]+.

Sources & evidence

ORD record
ord-5c3a6bd1587940b287ca94d5ef0bfb03
Source dataset
uspto-grants-2010_07
Patent number
US07754744B2

Reaction notes

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