Cyanamide → HCID 86711639, compound

HRID 527374Notes

Reaction equation

HRID 527374 reaction equation
BrN1C(=O)CCC1=O.[CH3:9][C:10]1[CH:11]=[C:12]([CH:38]=[CH:39][C:40]=1[S:41][CH3:42])[CH2:13][NH:14][C:15]([C:17]1[C:22](=[O:23])[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[C:20]([CH3:34])[N:19]([CH:35]([CH3:37])[CH3:36])[CH:18]=1)=[O:16].[N:43]#[C:44][NH2:45].CC(C)([O-])C.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CO>[CH3:9][C:10]1[CH:11]=[C:12]([CH:38]=[CH:39][C:40]=1[S:41]([CH3:42])=[N:45][C:44]#[N:43])[CH2:13][NH:14][C:15]([C:17]1[C:22](=[O:23])[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[C:20]([CH3:34])[N:19]([CH:35]([CH3:37])[CH3:36])[CH:18]=1)=[O:16]

Participants

7

Reactant 5

HCID 9864CyanamideHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 23665647Potassium tert-butoxideHCID 86711640HCID 86711640, compound

Product 1

HCID 86711639HCID 86711639, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Bromosuccinimide (63 mg, 0.35 mmol) is added to a mixture of 1-isopropyl-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 3-methyl-4-methylsulfanyl-benzylamide (preparation 66c, 115 mg, 0.24 mmol), cyanamide (14 mg, 0.33 mmol) and potassium tert-butoxide (32 mg, 0.29 mmol) in methanol (1.1 mL). After 20 min saturated aqueous sodium thiosulfate solution is added, and the mixture is extracted twice with dichloromethane. The combined organic layers is dried over Na2SO4 and concentrated under reduced pressure. The residue is directly used in the next step without further purification. Yield: 99 mg (80% of theory); ESI mass spectrum: [M+H]+=529; r.t. HPLC: 0.58 min (X012_S01).

Workup

  1. extractionthe mixture is extracted twice with dichloromethane
  2. dry with materialThe combined organic layers is dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is directly used in the next step without further purification
  5. customr.t
  6. custom0.58 min (X012_S01)

Sources & evidence

ORD record
ord-b54b09916df844278e25ecc839a0e625
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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