Potassium Cyanide → HCID 86661315, compound

HRID 1685088Notes

Reaction equation

HRID 1685088 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:9])=[N:4][C:3]=1[CH2:19][N:20]([CH3:30])[C:21]([C:23]1[C:24]([CH3:29])=[N:25][O:26][C:27]=1[CH3:28])=[O:22].[C:31]([Cu])#[N:32].[C-]#N.[K+]>CN(C=O)C.CCOC(C)=O>[C:31]([C:2]1[S:6][C:5]([NH:7][C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:9])=[N:4][C:3]=1[CH2:19][N:20]([CH3:30])[C:21]([C:23]1[C:24]([CH3:29])=[N:25][O:26][C:27]=1[CH3:28])=[O:22])#[N:32]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 86661316HCID 86661316, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86661315HCID 86661315, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Example: A mixture of 3,5-dimethyl-isoxazole-4-carboxylic acid {5-bromo-2-[3-(3-fluoro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amide (Ex. 151) (100 mg, 0.2 mmol), CuCN (180 mg, 2.0 mmol) and KCN (13 mg, 0.2 mmol) in DMF (1 mL) was heated to 120 C for 5 hours. Upon cooling the mix was diluted with EtOAc (50 mL), filtered, washed with brine, dried and evaporated. Flash chromatography afforded 3,5-dimethyl-isoxazole-4-carboxylic acid {5-cyano-2-[3-(3-fluoro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amide.

Workup

  1. temperaturewas heated to 120 C for 5 hours
  2. temperatureUpon cooling the mix
  3. filtrationfiltered
  4. washwashed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-b31047147b6542c5be48dce8b1ccbf7b
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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