6-(Piperidin-4-ylamino)-4-trifluoromethyl-nicotinic acid methyl ester dihydrochloride → 6-[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamide

HRID 913136Notes

Reaction equation

HRID 913136 reaction equation
CO[C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=3)[CH2:10][CH2:9]2)=[CH:5][C:4]=1[O:30][CH2:31][CH2:32]C.Cl.Cl.COC(=O)C1C(C(F)(F)F)=CC(NC2CCNCC2)=NC=1.[Cl:57]C1C=CC(C=O)=CC=1OCC>>[Cl:57][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=3)[CH2:10][CH2:9]2)=[CH:5][C:4]=1[O:30][CH2:31][CH3:32]

Participants

4

Reactant 3

HCID 426042136-(Piperidin-4-ylamino)-4-trifluoromethyl-nicotinic acid methyl ester dihydrochloride2×HCID 426049596-[1-(4-Methoxy-3-propoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamideHCID 547756424-Chloro-3-ethoxybenzaldehyde2×

Product 1

HCID 674006896-[1-(4-Chloro-3-ethoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamide

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 6-(piperidin-4-ylamino)-4-trifluoromethyl-nicotinic acid methyl ester dihydrochloride (intermediate B7) and 4-chloro-3-ethoxy-benzaldehyde (intermediate E2) in a yield of 13.1 mg (19%). MS (ISP): 458.3 [M+H]+.

Sources & evidence

ORD record
ord-b5f6485afb3a4805956da372341a24a9
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

Loading…