Ethanolamine → HCID 20773298, compound

HRID 1814803Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][N:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14](F)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C@H:5]([CH3:18])[CH2:4][N:3]1[C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22].[CH2:28]([CH2:30][NH2:31])[OH:29].[Cl-].[NH4+]>CN1CCCC1=O>[CH3:1][C@H:2]1[CH2:7][N:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:31][CH2:30][CH2:28][OH:29])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C@H:5]([CH3:18])[CH2:4][N:3]1[C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:22])[F:23]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (R)-[(2S,5R)-2-methyl-5-methyl-5-methyl-4-(4-fluorophenylsulphonyl)-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (Example 6, 350 mg, 0.85 mmol) in 1-methyl-2-pyrrolidone (2 ml) was added ethanolamine (114 mg, 1.87 mmol) and the mixture heated at 120° C. for 24 hours. The mixture was cooled to ambient temperature, poured onto saturated ammonium chloride solution (30 ml), the mixture extracted with diethyl ether (2×30 ml), the combined ether extracts washed with brine, dried and evaporated. The residue was chromatographed on silica with EtOAc as eluent to give the title compound as a solid (143 mg, 0.32 mmol). NMR: 0.95 (d, 3H), 1.55 (d, 3H), 1.6 (s, 3H), 3.1 (m, 2H), 3.3 (dt, 2H), 3.4 (d, 1H), 3.8 (dt, 2H), 4.2 (s, 1H), 4.6 (m, 2H), 6.6 (d, 2H), 7.5 (d, 2H); m/z 411.

Workup

temperatureThe mixture was cooled to ambient temperature
extractionthe mixture extracted with diethyl ether (2×30 ml)
washthe combined ether extracts washed with brine
customdried
customevaporated
customThe residue was chromatographed on silica with EtOAc as eluent

Sources & evidence

ORD record: ord-9be6e0d7e65b4c7f8a0f2b548e3f1e51
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878712B1

Reaction notes

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