Cyanogen Bromide → HCID 25267750, compound

HRID 1516398Notes

Reaction equation

HRID 1516398 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[NH:29])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1.[N:31]#[C:32]Br>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[N:29][C:32]#[N:31])=[O:28])=[CH:23][CH:22]=2)=[O:20])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 25267402HCID 25267402, compound

Product 1

HCID 25267750HCID 25267750, compoundYield 37.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
27.5 °C

Procedure

To a stirring solution of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-methyl sulfoximide (50 mg, 0.000108 mol) and DMAP (14.5 mg, 0.000216 mol) in DCM (1 mL) was added cyanogen bromide (23 mg, 0.000216 mol) at 25° C. Reaction mixture was stirred at 25-30° C. for 18 hr and then diluted with DCM (10 mL). Organic layer was washed with dil.HCl. Drying over sodium sulfate and evaporation afforded 20 mg of titled compound in 37% yield.

Workup

  1. customReaction mixture
  2. washOrganic layer was washed with dil
  3. dry with materialDrying over sodium sulfate and evaporation

Sources & evidence

ORD record
ord-37218938351f475db551d85d1721d4cd
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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