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

HRID 502427Notes

Reaction equation

HRID 502427 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[C:21]([O:23][CH2:24][CH3:25])[C:20](F)=[C:19]([O:27][CH2:28][CH3:29])[CH:18]=3)[CH2:12][CH2:11]2)=[O:8])[CH:5]=1.C(OC1C=C(C=C(OCC)C=1[N:47]1[CH:51]=[CH:50][CH:49]=[CH:48]1)C=O)C.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:35])[C:4]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[C:21]([O:23][CH2:24][CH3:25])[C:20]([N:47]4[CH:51]=[CH:50][CH:49]=[CH:48]4)=[C:19]([O:27][CH2:28][CH3:29])[CH:18]=3)[CH2:12][CH2:11]2)=[O:8])[CH:5]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 534860133,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehydeHCID 68458070N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-5-methoxy-isophthalamic acid methyl ester

Product 1

HCID 68457949N-[1-(3,5-Diethoxy-4-pyrrol-1-yl-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 (example 143) was reacted with 3,5-diethoxy-4-pyrrol-1-yl-benzaldehyde (example 40b), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as light yellow solid. MS: 536.5 (MH+).

Sources & evidence

ORD record
ord-1031069a3d9d48cda8d697d940ee137e
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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