Cyanamide → HCID 178486145, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[N:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Br:17])=[C:4]([O:18][Si](C(C)(C)C)(C)C)[C:3]=1[S:26]([N:29]([CH3:31])[CH3:30])(=[O:28])=[O:27].[N:32]#[C:33]N.C([N:38](CC)C(C)C)(C)C.[F-].[Cs+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:33]#[N:32])[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Br:17])=[NH:38])=[C:4]([OH:18])[C:3]=1[S:26]([N:29]([CH3:30])[CH3:31])(=[O:28])=[O:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2-bromophenyl)carbodiimide (266 mg, 0.49 mmol) in acetonitrile (5 mL) at room temperature, cyanamide (83 mg, 1.96 mmol) and N,N-diisopropylethylamine (76 mg, 0.59 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with a mixture of THF (3 mL) and methanol (1 mL). Cesium fluoride (90 mg, 0.59 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by Gilson HPLC to give the desired product (70 mg, 30%). EI-MS m/z 473.75(M+).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionThe residue was diluted with a mixture of THF (3 mL) and methanol (1 mL)
- stirringThe reaction mixture was stirred at 0° C. for 3 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- customThe residue was purified by Gilson HPLC
Sources & evidence
- ORD record
- ord-05875caedfc64b1faad04da37088892e
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680317B2
Reaction notes
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