Potassium Carbonate → HCID 66785305, compound

HRID 1095403Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1:5-(1-hydroxy-2-cyclohexylcarbonylamino-2-tetrahydropyran-4-ylethyl)-2-thioxo-1,3,4-oxadiazoline (prepared in step 1 of example 8; 281 mg) in N,N-dimethylformamide (2 ml) were added N-methyl-N-(1,1-dimethyl-2-chloroethyl)amine (125 mg) and potassium carbonate (328 mg) and the mixture was stirred for 3 hours at 70° C. The reaction mixture was poured into brine and was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=9:1) to give N′-(3,4,4-trimethyl-1,3-thiazolidin-2-ylidene)-[3-cyclohexylcarbonylamino-3-(tetrahydropyran-4-yl)-2-hydroxypropanohydrazide] (279 mg).

Workup

extractionwas extracted with ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record: ord-454f4c1504c84c4dbb76cfe3df384d5f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138182B2

Reaction notes

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