Trifluoroacetic acid → N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-5-methoxy-isophthalamic acid methyl ester

HRID 502426Notes

Reaction equation

HRID 502426 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:8])[CH:5]=1.COC(=O)C1C=C(OC)C=C(C(O)=O)C=1.C(OC(N1CCC(N)CC1)=O)(C)(C)C.ClC1N=C(OC)N=C(OC)N=1.C(O)(C(F)(F)F)=O.[CH2:69]([O:71][C:72]1[CH:73]=[C:74]([CH:77]=[C:78]([O:81][CH2:82][CH3:83])[C:79]=1[F:80])[CH:75]=O)[CH3:70].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:6]([C:7]([NH:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:75][C:74]3[CH:77]=[C:78]([O:81][CH2:82][CH3:83])[C:79]([F:80])=[C:72]([O:71][CH2:69][CH3:70])[CH:73]=3)[CH2:14][CH2:15]2)=[O:8])[CH:5]=1

Participants

11

Reactant 8

HCID 6422Trifluoroacetic acidHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 5003444Sodium cyanoborohydrideHCID 110201363-Methoxy-5-(methoxycarbonyl)benzoic acidHCID 591282733,5-Diethoxy-4-fluoro-benzaldehydeHCID 684569895-methoxy-N-piperidin-4-yl-isophthalamic acid methyl ester

Product 1

HCID 68458070N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-5-methoxy-isophthalamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 5-methoxy-N-piperidin-4-yl-isophthalamic acid methyl ester [prepared from 5-methoxy-isophthalic acid monomethyl ester (Synthetic Communications, 31(12), 1921-1926; 2001) by condensation with 4-amino-piperidine-carboxylic acid tert-butyl ester, using acid activation with 2-chloro-4,6-dimethoxy-1,3,5-triazine in analogy to the procedure described in example 50 h) followed by Boc cleavage with TFA in analogy to the procedure described in example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 489.3 (MH+).

Workup

  1. customdescribed in example 50 h

Sources & evidence

ORD record
ord-3c9b203f35a8420294c5ef70e6306978
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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