Methyl 5-methoxy-3-oxopentanoate → HCID 67072257, compound

HRID 1242431Notes

Reaction equation

HRID 1242431 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][C:10]=1[CH3:17])([CH3:7])[CH3:6])[CH3:2].[CH3:19][O:20][CH2:21][CH2:22][C:23]1[C:28]([C:29](O)=[O:30])=[CH:27][N:26]=[C:25]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[N:24]=1.COC(=O)CC(=O)CCOC>>[CH2:1]([O:3][C:4](=[O:18])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:29]([C:28]2[C:23]([CH2:22][CH2:21][O:20][CH3:19])=[N:24][C:25]([C:32]3[CH:33]=[CH:34][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:36][CH:37]=3)=[N:26][CH:27]=2)=[O:30])=[CH:11][C:10]=1[CH3:17])([CH3:6])[CH3:7])[CH3:2]

Participants

4

Reactant 3

HCID 542416Methyl 5-methoxy-3-oxopentanoateHCID 219356384-(2-Methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acidHCID 23563108HCID 23563108, compound

Product 1

HCID 67072257HCID 67072257, compound

Procedure

In analogy to the procedures described in example 26B] and 26C], 2-(4-aminomethyl-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (example 97B]) was reacted with 4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid (prepared from 5-methoxy-3-oxo-pentanoic acid methyl ester, in analogy to the procedures described in examples 27C] and 27D] followed by saponification in analogy to the procedure described in example 53B]) to give 2-[4-({[4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-2-methyl-phenoxy]-2-methyl-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as light yellow oil.

Sources & evidence

ORD record
ord-c125e180395648f99924e13da1d1b9bd
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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