Diisopropylethylamine → 2-{3-[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenoxy}-2-methyl-propionic acid ethyl ester

HRID 502404Notes

Reaction equation

HRID 502404 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([O:8][C:9]1[CH:14]=[C:13]([C:15](=[O:23])[NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:12]=[C:11]([O:24][CH3:25])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[CH2:27]([O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH:33]=O)[CH3:28].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:26])[C:5]([O:8][C:9]1[CH:10]=[C:11]([O:24][CH3:25])[CH:12]=[C:13]([C:15](=[O:23])[NH:16][CH:17]2[CH2:18][CH2:19][N:20]([CH2:33][C:32]3[CH:35]=[CH:36][C:37]([O:38][CH3:39])=[C:30]([O:29][CH2:27][CH3:28])[CH:31]=3)[CH2:21][CH2:22]2)[CH:14]=1)([CH3:6])[CH3:7])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 684567162-[3-Methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-2-methyl-propionic acid ethyl ester

Product 1

HCID 684572152-{3-[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenoxy}-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 2-[3-methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-2-methyl-propionic acid ethyl ester (example 66b) was reacted with 3-ethoxy-4-methoxybenzaldehyde, sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as off-white amorphous solid. MS: 529.3 (MH+).

Sources & evidence

ORD record
ord-30683a5a609c449ba3a206e8fa876e41
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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