6-(Piperidin-4-ylamino)-4-trifluoromethyl-nicotinic acid methyl ester dihydrochloride → 6-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinamide

HRID 2355608Notes

Reaction equation

HRID 2355608 reaction equation
COC1C=CC(C[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)=CC=1OCCC.Cl.Cl.COC(=O)C1C(C(F)(F)F)=CC(NC2CCNCC2)=NC=1.[CH2:57]([O:59][C:60]1[CH:61]=[C:62]([CH:65]=[C:66]([O:69][CH2:70][CH3:71])[C:67]=1[F:68])[CH:63]=O)[CH3:58]>>[CH2:57]([O:59][C:60]1[CH:61]=[C:62]([CH:65]=[C:66]([O:69][CH2:70][CH3:71])[C:67]=1[F:68])[CH2:63][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:23]=[C:22]([C:24]([F:26])([F:25])[F:27])[C:18]([C:19]([NH2:21])=[O:20])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[CH3:58]

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 591282733,5-Diethoxy-4-fluoro-benzaldehyde2×

Product 1

HCID 674006916-[1-(3,5-Diethoxy-4-fluoro-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 3,5-diethoxy-4-fluoro-benzaldehyde (intermediate E5) in a yield of 2.3 mg (3%). MS (ISP): 485.3 [M+H]+.

Sources & evidence

ORD record
ord-5f3558776ac348d5944fd1dc9febc02c
Source dataset
uspto-grants-2010_07
Patent number
US07754744B2

Reaction notes

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