Water → HCID 69515816, compound

HRID 1178552Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:14]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:16][CH2:15]2)[S:12][CH:13]=1.[Li+].CCC[CH2-].[C:30](Cl)(=[O:32])[CH3:31].O>C1COCC1.CCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:14]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:15][CH2:16]2)[S:12][C:13]=1[C:30](=[O:32])[CH3:31]

Participants

Conditions

Temperature: -78 °C

Procedure

4-(2,4-Dichloro-phenyl)-2-[1-(2-methoxy-phenyl)-cyclopropyl]-thiazole (30 mg, 0.079 mmol) was dissolved in 1 mL of dry THF and the solution was cooled to −78° C. N-butyllithium (0.044 mL, 0.088 mmol) was added dropwise as a commercial 2M solution in pentane and the reaction stirred for 30 min at −78° C. Acetylchloride (0.056 mL, 0.79 mmol) was added as a neat liquid and the reaction warmed to room temperature with stirring over 1h. Water (1 volume equivalent relative to THF) was added and the THF removed in vacuo. The crude material was then dissolved in 1:1 methanol/DMSO (2 volume equivalents relative to THF) and the desired product purified by reversed phase HPLC/MS using an acetonitrile/water gradient and C18 stationary phase. Yield: 4.4 mg (14%). [MH]+ 418.2, 420.2.

Workup

temperaturethe reaction warmed to room temperature
stirringwith stirring over 1h
customthe THF removed in vacuo
dissolutionThe crude material was then dissolved in 1:1 methanol/DMSO (2 volume equivalents relative to THF)
customthe desired product purified by reversed phase HPLC/MS

Sources & evidence

ORD record: ord-1ff6e01bf0684946876e63d5da8afc35
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276526B2

Reaction notes

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