Potassium Carbonate → HCID 58505816, compound

HRID 1917608Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:11]([CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:12]([C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[N:13]3[C:18]=2[CH:17]=[CH:16][C:15]([OH:19])=[CH:14]3)=[O:9])=[CH:4][CH:3]=1.Cl.Cl[CH2:37][C:38]1[S:39][C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[S:39]1[C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=[C:38]1[CH2:37][O:19][C:15]1[CH:16]=[CH:17][C:18]2[N:13]([C:12]([C:20](=[O:25])[C:21]([CH3:23])([CH3:24])[CH3:22])=[C:11]([CH2:26][C:27]([CH3:33])([CH3:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:10]=2[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:9])[CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of ethyl 3-{1-[(4-chlorophenyl)carbonyl]-3-(2,2-dimethylpropanoyl)-6-hydroxyindolizin-2-yl}-2,2-dimethylpropanoate (85.0 mg, 0.176 mmol), 2-(chloromethyl)-1,3-benzothiazole-HCl (60.1 mg, 0.263 mmol), and potassium carbonate (97.1, 0.703 mmol) in DMF (3.0 mL) is stirred at 50° C. for 1 h. The mixture is cooled to 23° C. then filtered, concentrated in vacuo, and purified by flash chromatography (SiO2, hexanes to 1:1 hexanes:EtOAc) to yield ethyl 3-[6-(1,3-benzothiazol-2-ylmethoxy)-1-[(4-chlorophenyl)carbonyl]-3-(2,2-dimethylpropanoyl)indolizin-2-yl]-2,2-dimethylpropanoate (74 mg, 67%).

Workup

temperatureThe mixture is cooled to 23° C.
filtrationthen filtered
concentrationconcentrated in vacuo
custompurified by flash chromatography (SiO2, hexanes to 1:1 hexanes:EtOAc)

Sources & evidence

ORD record: ord-4c48c325fe484ab590065a987fe3fc2d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

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