Potassium Hydroxide → HCID 178487683, compound

HRID 1803705Notes

Reaction equation

[OH-].[K+].[C:3]([C:6]1[C:11]([NH:12][C:13]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[S:18][CH:19]=2)=O)=[C:10]([CH3:26])[C:9]([O:27][CH3:28])=[CH:8][CH:7]=1)(=[O:5])[CH3:4]>N1C=CC=CC=1.CCO>[CH:20]1([C:17]2[S:18][CH:19]=[C:15]([C:13]3[CH:4]=[C:3]([OH:5])[C:6]4[C:11](=[C:10]([CH3:26])[C:9]([O:27][CH3:28])=[CH:8][CH:7]=4)[N:12]=3)[N:16]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

Conditions

Temperature: 150 °C

Procedure

Freshly grounded KOH (2 mmol, 112 mg) was added to a solution of 2-cyclohexyl-thiazole-4-carboxylic acid (6-acetyl-3-methoxy-2-methylphenyl)amide (118, 373 mg, 2 mmol) in pyridine (20 mL). The mixture was divided into several batches and each batch was individually heated by microwave irradiation at 150° C. for 30 min. Then, the different batches were combined and pyridine was evaporated. The residue was treated with aqueous citric acid to give a suspension, which was subsequently diluted with a small volume of EtOH, then partitioned between water and CH2Cl2. Organic layer was dried (Na2SO4), and evaporated. The residue was purified by column chromatography (gradient of CH2Cl2:MeOH, 1:0 to 93:7) to give 1.8 g (72.5%) of the title compound 119 as a white powder: m/z=355 (M+H)+.

Workup

custompyridine was evaporated
additionThe residue was treated with aqueous citric acid
customto give a suspension, which
custompartitioned between water and CH2Cl2
dry with materialOrganic layer was dried (Na2SO4)
customevaporated
customThe residue was purified by column chromatography (gradient of CH2Cl2:MeOH, 1:0 to 93:7)

Sources & evidence

ORD record: ord-43f6ade3327643729fb71af7b05fae2d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349869B2

Reaction notes

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