4-Methoxy-3-propoxybenzaldehyde → 6-[1-(4-Methoxy-3-propoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinic acid

HRID 913140Notes

Reaction equation

HRID 913140 reaction equation
C(OC1C=C(C=CC=1O)C[N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)C.Cl.Cl.COC(=O)C1C(C(F)(F)F)=CC(NC2CCNCC2)=NC=1.[CH3:55][O:56][C:57]1[CH:64]=[CH:63][C:60]([CH:61]=O)=[CH:59][C:58]=1[O:65][CH2:66][CH2:67][CH3:68]>>[CH3:55][O:56][C:57]1[CH:64]=[CH:63][C:60]([CH2:61][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[CH:23]=[C:22]([C:24]([F:26])([F:25])[F:27])[C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]=3)[CH2:10][CH2:9]2)=[CH:59][C:58]=1[O:65][CH2:66][CH2:67][CH3:68]

Participants

4

Reactant 3

HCID 5921094-Methoxy-3-propoxybenzaldehydeHCID 426042136-(Piperidin-4-ylamino)-4-trifluoromethyl-nicotinic acid methyl ester dihydrochloride2×HCID 674010866-[1-(3-Ethoxy-4-hydroxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinic acid

Product 1

HCID 674002816-[1-(4-Methoxy-3-propoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinic acid

Procedure

The title compound was prepared in analogy to the synthesis of 6-[1-(3-ethoxy-4-hydroxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinic acid (example 201) from 6-(piperidin-4-ylamino)-4-trifluoromethyl-nicotinic acid methyl ester dihydrochloride (intermediate B7) and 4-methoxy-3-propoxy-benzaldehyde (intermediate E11) in a yield of 16.4 mg (23%). MS (ISP): 468.3 [M+H]+.

Sources & evidence

ORD record
ord-41c43ce9eeb54dabaa2fd252991f415d
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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