Potassium Carbonate → HCID 178489415, compound

HRID 1774710Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][C:16]=2[C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[N:10]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][C:16]=2[C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)[NH:11][N:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of (23) (50 mg, 0.108 mmol) in methanol (5 mL) and water (5 mL) was added potassium carbonate (29 mg, 0.216 mmol). The RM was heated to 60° C. overnight. After completion of the SM, the solvents were completely distilled off and diluted with water and extracted with chloroform twice. The organic layer was dried over sodium sulphate and completely distilled off to get the crude product, which was passed through 100-200 mesh silica gel eluting the pre compound at 28-30% ethyl acetate in hexane as eluent to get the pale yellow colored solid (24). 1H NMR (CDCl3) δ: 11.05 (1H), 8.57 (d, J=4.75 1H), 7.50 (m, J=5.85 1H), 7.48 (m, J=5.73 1H), 7.16 (m, J=4.87 1H), 7.12 (m, J=3.17 1H), 6.98 (m, J=4.87 3H), 6.61 (d, J=8.17 1H), 3.21 (3H) and MS m/z=308.1.

Workup

distillationAfter completion of the SM, the solvents were completely distilled off
additiondiluted with water
extractionextracted with chloroform twice
dry with materialThe organic layer was dried over sodium sulphate
distillationcompletely distilled off
customto get the crude product, which

Sources & evidence

ORD record: ord-cb63c4041d4c4a5a86461c68d29c9f63
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260426B2

Reaction notes

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