Ethanolamine → 1-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-3-(2-hydroxy-ethyl)-urea

HRID 2247361Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([N:17]=[C:18]=[O:19])=[N:14][C:13]=2[CH3:20])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[NH2:21][CH2:22][CH2:23][OH:24]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH:17][C:18]([NH:21][CH2:22][CH2:23][OH:24])=[O:19])=[N:14][C:13]=2[CH3:20])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

5-(3-fluoro-4-methanesulfonyl-phenyl)-2-isocyanato-4-methyl-thiazole (88a)(0.58 mmol, 0.183 g) is dissolved in dioxane (5 ml) and treated with 2-aminoethanol (0.64 mmol, 0.039 ml) under argon. The reaction mixture is stirred and heated to 80° C. for 1 hour. The solvent is then removed and the residue dissolved in EtOAc and washed with water (2×20 ml) followed by brine (20 ml) and dried over MgSO4. After filtration, the solvent is removed in vacuo and the residue purified by chromatography on silica eluting with ethyl acetate—methanol (9:1) to give the title compound.

Workup

customThe solvent is then removed
dissolutionthe residue dissolved in EtOAc
washwashed with water (2×20 ml)
dry with materialdried over MgSO4
filtrationAfter filtration
customthe solvent is removed in vacuo
customthe residue purified by chromatography on silica eluting with ethyl acetate—methanol (9:1)

Sources & evidence

ORD record: ord-9315e7cb562a4064b8b01993cbe735dc
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687637B2

Reaction notes

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