Cyanoacetamide → HCID 58922510, compound

HRID 639164Notes

Reaction equation

HRID 639164 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[CH:7]([C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)=O.[F:17][C:18]([F:39])([F:38])[C:19]1[CH:20]=[C:21]([NH:25][C:26]([CH3:37])=[CH:27][C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH:22]=[CH:23][CH:24]=1.N1CCCCC1>C(O)C>[CH3:35][Si:33]([CH3:34])([CH3:36])[CH2:32][CH2:31][O:30][C:28]([C:27]1[CH:7]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[C:3]([C:4]([NH2:6])=[O:5])=[C:1]([NH2:2])[N:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:38])([F:17])[F:39])[CH:20]=2)[C:26]=1[CH3:37])=[O:29]

Participants

6

Reactant 4

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 68428569HCID 68428569, compound

Product 1

HCID 58922510HCID 58922510, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 0.45 g (5.40 mmol) 2-cyanoacetamide in 5 ml ethanol are added 0.71 g (5.40 mmol) 4-formylbenzonitrile, a solution of 1.87 g (5.40 mmol) of the compound of Example 40A in 6 ml ethanol and 0.16 g (1.89 mmol) piperidine. The mixture is stirred under reflux for 3.5 hours. The reaction mixture is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 2000 μl; number of injections: 8). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. customThe reaction mixture is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 2000 μl; number of injections: 8)
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae34c1f606ac45909c1ec72bedb4faa5
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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