6-[1-(4-Methoxy-3-propoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamide → 5-[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-pyrazine-2-carboxylic acid amide

HRID 913142Notes

Reaction equation

HRID 913142 reaction equation
COC1C=CC(C[N:8]2CCC(NC3C=C(C(F)(F)F)C(C(N)=O)=CN=3)CC2)=CC=1OCCC.Cl.Cl.CO[C:38]([C:40]1[CH:45]=[N:44][C:43]([NH:46][CH:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)=[CH:42][N:41]=1)=[O:39].[Cl:53][C:54]1[CH:61]=[CH:60][C:57]([CH:58]=O)=[CH:56][C:55]=1[O:62][CH2:63][CH3:64]>>[Cl:53][C:54]1[CH:61]=[CH:60][C:57]([CH2:58][N:50]2[CH2:49][CH2:48][CH:47]([NH:46][C:43]3[N:44]=[CH:45][C:40]([C:38]([NH2:8])=[O:39])=[N:41][CH:42]=3)[CH2:52][CH2:51]2)=[CH:56][C:55]=1[O:62][CH2:63][CH3:64]

Participants

4

Reactant 3

HCID 426049596-[1-(4-Methoxy-3-propoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamideHCID 547756424-Chloro-3-ethoxybenzaldehyde2×HCID 673996095-(Piperidin-4-ylamino)-pyrazine-2-carboxylic acid methyl ester dihydrochloride

Product 1

HCID 674014455-[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-pyrazine-2-carboxylic acid amide

Procedure

The title compound was prepared in analogy to the synthesis of 6-[1-(4-methoxy-3-propoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamide (example 197) from 5-(piperidin-4-ylamino)-pyrazine-2-carboxylic acid methyl ester dihydrochloride (intermediate B14) and 4-chloro-3-ethoxy-benzaldehyde (intermediate E2) in a yield of 12.1 mg (21%). MS (ISP): 390.3 [M+H]+.

Sources & evidence

ORD record
ord-d3f5acbc86b247489ffa127a2d8bd800
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

Loading…