Potassium Carbonate → HCID 66785305, compound

HRID 1441954Notes

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-(tetrah ydropyran-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-b5de47da23c54aef807840b13dd529a3
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655804B2

Reaction notes

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