Sodium Cyanide → HCID 18387429, compound

HRID 2296751Notes

Reaction equation

CS([CH2:5][CH2:6][CH:7]1[CH:13]=[CH:12][N:11]([C:14](=[O:36])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:35])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:17][CH:16]=2)[C:10]2[CH:37]=[CH:38][CH:39]=[CH:40][C:9]=2[S:8]1)(=O)=O.[C-:41]#[N:42].[Na+]>CN(C)C=O>[C:41]([CH2:5][CH2:6][CH:7]1[CH:13]=[CH:12][N:11]([C:14](=[O:36])[C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:35])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:19][CH:20]=2)[C:10]2[CH:37]=[CH:38][CH:39]=[CH:40][C:9]=2[S:8]1)#[N:42]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of Compound 16 as prepared in Example 11 (0.115 g, 0.197 mM) and sodium cyanide (20 mg) in dimethylformamide was stirred in a 70° C. oil bath for 4 hours. The reaction mixture was then cooled to RT and the DMF was removed under reduced pressure. The residual semi-solid was diluted with water (30 ml) and extracted with ethyl acetate (2×30 ml). The combined ethyl acetate extracts were dried (MgSO4) , filtered and evaporated in vacuo. The crude mixture was purified by chromatography to give pure product as a white solid (71 mg, 70%). m/z (MH+)518

Workup

temperatureThe reaction mixture was then cooled to RT
customthe DMF was removed under reduced pressure
additionThe residual semi-solid was diluted with water (30 ml)
extractionextracted with ethyl acetate (2×30 ml)
dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
filtrationfiltered
customevaporated in vacuo
customThe crude mixture was purified by chromatography

Sources & evidence

ORD record: ord-9452359a33324e56bc824a5f30f4f166
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489321B1

Reaction notes

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