Formaldehyde → (4-{Methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

HRID 1393091Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH3:30])=[CH:9][CH:8]=1)[CH3:2].[CH2:32]=O>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:32])[CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=3)=[N:17][C:16]=2[CH3:30])=[CH:9][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (4-{[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester (0.09 g, 0.2 mmol) in dioxane (1 mL) was treated with 1N NaH2PO3 solution (1 ml) and a 37% aqueous solution of formaldehyde (1 ml). The mixture was heated to 60° C. for 7.5 h. Additional dioxane (1 ml) was added and heated for 11.5 h. The mixture was extracted with aqueous saturated NaHCO3 solution/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 0.08 g (86%) of (4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester as yellow waxy solid, MS: 465 (MH+).

Workup

temperatureheated for 11.5 h
extractionThe mixture was extracted with aqueous saturated NaHCO3 solution/Et2O (3×)
washThe organic phases were washed with aqueous 10% NaCl
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-297cdcf8916d4c05ba0810971f55ac28
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345067B2

Reaction notes

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