N-{3-[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-phenyl}-acetamide → 5-[1-(2,6-Diethoxy-4'-fluoro-biphenyl-4-ylmethyl)-piperidin-4-ylamino]-pyrazine-2-carboxylic acid methyl ester

HRID 913146Notes

Reaction equation

HRID 913146 reaction equation
ClC1C=CC(CN2CCC(NC3C=C(NC(=O)C)C=CC=3)CC2)=CC=1OCC.Cl.Cl.[CH3:31][O:32][C:33]([C:35]1[CH:40]=[N:39][C:38]([NH:41][CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:37][N:36]=1)=[O:34].[CH2:48]([O:50][C:51]1[CH:56]=[C:55]([CH:57]=O)[CH:54]=[C:53]([O:59][CH2:60][CH3:61])[C:52]=1[C:62]1[CH:67]=[CH:66][C:65]([F:68])=[CH:64][CH:63]=1)[CH3:49]>>[CH3:31][O:32][C:33]([C:35]1[CH:40]=[N:39][C:38]([NH:41][CH:42]2[CH2:47][CH2:46][N:45]([CH2:57][C:55]3[CH:54]=[C:53]([O:59][CH2:60][CH3:61])[C:52]([C:62]4[CH:67]=[CH:66][C:65]([F:68])=[CH:64][CH:63]=4)=[C:51]([O:50][CH2:48][CH3:49])[CH:56]=3)[CH2:44][CH2:43]2)=[CH:37][N:36]=1)=[O:34]

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 673996095-(Piperidin-4-ylamino)-pyrazine-2-carboxylic acid methyl ester dihydrochloride

Product 1

HCID 674009385-[1-(2,6-Diethoxy-4'-fluoro-biphenyl-4-ylmethyl)-piperidin-4-ylamino]-pyrazine-2-carboxylic acid methyl ester

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 5-(piperidin-4-ylamino)-pyrazine-2-carboxylic acid methyl ester dihydrochloride (intermediate B14) and 2,6-diethoxy-4′-fluoro-biphenyl-4-carbaldehyde (intermediate E22) in a yield of 5.8 mg (7%). MS (ISP): 509.4 [M+H]+.

Sources & evidence

ORD record
ord-1d9d7d021e9445be9f9e636f6048250a
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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