Cyanamide → HCID 86711636, compound

HRID 527368Notes

Reaction equation

HRID 527368 reaction equation
[CH:1]1([S:4][C:5]2[CH:35]=[CH:34][C:8]([CH2:9][NH:10][C:11]([C:13]3[C:18](=[O:19])[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)=[C:16]([CH3:30])[N:15]([CH:31]([CH3:33])[CH3:32])[CH:14]=3)=[O:12])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.[N:36]#[C:37][NH2:38].BrN1C(=O)CCC1=O.CC(C)([O-])C.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CO>[CH:1]1([S:4]([C:5]2[CH:35]=[CH:34][C:8]([CH2:9][NH:10][C:11]([C:13]3[C:18](=[O:19])[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)=[C:16]([CH3:30])[N:15]([CH:31]([CH3:32])[CH3:33])[CH:14]=3)=[O:12])=[CH:7][CH:6]=2)=[N:38][C:37]#[N:36])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 9864CyanamideHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 23665647Potassium tert-butoxideHCID 73296561HCID 73296561, compound

Product 1

HCID 86711636HCID 86711636, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-isopropyl-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 4-cyclopropylsulfanyl-benzylamide (preparation 63c, 75 mg, 0.15 mmol), cyanamide (8 mg, 0.19 mmol), N-bromosuccinimide (40 mg, 0.22 mmol) and potassium tert-butoxide (20 mg, 0.18 mmol) in methanol (1 mL) is stirred at room temperature for 1 h. Saturated aqueous sodium thiosulfate solution is added, and the mixture is extracted twice with dichloromethane. The organic layer is dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by preparative reversed phase HPLC (Xbridge, gradient of acetonitrile in water, 0.1% NH3). Yield: 7 mg (8% of theory); ESI mass spectrum: [M+H]+=541; r.t. HPLC: 0.64 min (X012_S02).

Workup

  1. extractionthe mixture is extracted twice with dichloromethane
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by preparative reversed phase HPLC (Xbridge, gradient of acetonitrile in water, 0.1% NH3)
  5. customr.t
  6. custom0.64 min (X012_S02)

Sources & evidence

ORD record
ord-6da4734fd4714bfca7a4d0028c9ecf30
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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