4-Methoxy-3-(2-methylpropoxy)benzaldehyde → 6-[1-(3-Isobutoxy-4-methoxy-benzyl)-piperidin-4-ylamino]-4-trifluoromethyl-nicotinic acid

HRID 913141Notes

Reaction equation

HRID 913141 reaction equation
C(OC1C=C(C=CC=1O)CN1CCC(NC2C=C(C(F)(F)F)C(C(O)=O)=CN=2)CC1)C.Cl.Cl.C[O:35][C:36](=[O:54])[C:37]1[C:42]([C:43]([F:46])([F:45])[F:44])=[CH:41][C:40]([NH:47][CH:48]2[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)=[N:39][CH:38]=1.[CH2:55]([O:59][C:60]1[CH:61]=[C:62]([CH:65]=[CH:66][C:67]=1[O:68][CH3:69])[CH:63]=O)[CH:56]([CH3:58])[CH3:57]>>[CH2:55]([O:59][C:60]1[CH:61]=[C:62]([CH:65]=[CH:66][C:67]=1[O:68][CH3:69])[CH2:63][N:51]1[CH2:50][CH2:49][CH:48]([NH:47][C:40]2[CH:41]=[C:42]([C:43]([F:44])([F:45])[F:46])[C:37]([C:36]([OH:35])=[O:54])=[CH:38][N:39]=2)[CH2:53][CH2:52]1)[CH:56]([CH3:57])[CH3:58]

Participants

4

Reactant 3

HCID 24141104-Methoxy-3-(2-methylpropoxy)benzaldehydeHCID 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 673999766-[1-(3-Isobutoxy-4-methoxy-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 3-isobutoxy-4-methoxy-benzaldehyde (intermediate E12) in a yield of 9.0 mg (12%). MS (ISP): 482.3 [M+H]+.

Sources & evidence

ORD record
ord-14de9fdae25f4b99b437670a8adb8877
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

Loading…