Dimethylformamide → HCID 20781271, compound

HRID 2181272Notes

Reaction equation

HRID 2181272 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:35])=[C:6]([C:8]2([S:22]([C:25]3[CH:26]=[N:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=3)(=[O:24])=[O:23])[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])[CH2:10][CH2:9]2)[CH:7]=1.[Cu](C#N)[C:37]#[N:38].CN(C)C=O>N1C=CC=CC=1.C(OCC)(=O)C.O>[C:37]([C:2]1[CH:3]=[CH:4][C:5]([F:35])=[C:6]([C:8]2([S:22]([C:25]3[CH:26]=[N:27][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:29][CH:30]=3)(=[O:24])=[O:23])[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]([F:20])([F:19])[F:21])(=[O:17])=[O:16])[CH2:10][CH2:9]2)[CH:7]=1)#[N:38]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 20781270HCID 20781270, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 20781271HCID 20781271, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A solution of the compound prepared in Example 75 (45 mg) was treated with copper cyanide (4 equivalents), pyridine (1 drop) and dimethylformamide (3 ml) and heated at 180° C. overnight. The reaction was diluted with ethyl acetate and water and filtered. The organic layer of the filtrate was washed with water and brine and dried, filtered and evaporated in vacuo. Purification by column chromatography gave the nitrile (27 mg, 66%). M/Z=559 (MH+).

Workup

  1. filtrationfiltered
  2. washThe organic layer of the filtrate was washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-b88039147a8145c788a8970de6ba400d
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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