Cyanogen Bromide → HCID 87543951, compound

HRID 1972298Notes

Reaction equation

HRID 1972298 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][NH:15][C:14]3=[N:28][C:29]#[N:30])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.Br[C:34]#[N:35].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:25])[F:27])[CH:19]=4)[CH2:16][N:15]([C:34]#[N:35])[C:14]3=[N:28][C:29]#[N:30])=[CH:11][CH:12]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 178512072HCID 178512072, compound

Product 1

HCID 87543951HCID 87543951, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)—N-(1-(4-(4-chlorophenoxy)phenyl)-5-(3-(trifluoromethyl)-phenyl)imidazolidin-2-ylidene)cyanamide [prepared from Example 203] (15.0 mg, 0.033 mmol) in 1,4-dioxane (0.5 mL) is treated with excess BrCN and K2CO3. The reaction mixture is heated at 100° C. for 2 h, cooled, then quenched with H2O (5 mL) and extracted with EtOAc (3×3 mL). The combined organics are evaporated en vacuo and purified by preparatory LC/MS followed by preparatory TLC to provide the title compound; HPLC-MS calculated for C24H15ClF3N5O (M+H+) 482.1, found 482.1.

Workup

  1. temperaturecooled
  2. customquenched with H2O (5 mL)
  3. extractionextracted with EtOAc (3×3 mL)
  4. customThe combined organics are evaporated en vacuo
  5. custompurified by preparatory LC/MS

Sources & evidence

ORD record
ord-0ac56ea7dfe441e990354a1e9a90c18e
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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