2-Amino-2-cyanoacetamide → 5-Amino-2-(quinolin-6-ylamino)thiazole-4-carboxamide

HRID 512539

Reaction equation

HRID 512539 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)=[C:2]=[S:3].[NH2:14][CH:15]([C:19]#[N:20])[C:16]([NH2:18])=[O:17]>CCOC(C)=O>[NH2:20][C:19]1[S:3][C:2]([NH:1][C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[CH:7]3)=[N:14][C:15]=1[C:16]([NH2:18])=[O:17]

Participants

4

Reactant 2

HCID 983412-Amino-2-cyanoacetamideHCID 137184226-Isothiocyanatoquinoline

Product 1

HCID 867033765-Amino-2-(quinolin-6-ylamino)thiazole-4-carboxamideYield 65.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-isothiocyanatoquinoline (0.50 g, 2.7 mmol) and 2-amino-cyanoacetamide (0.26g, 2.68 mmol) in EtOAc (20 mL) was refluxed for 90 min. The reaction mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography eluted with 2% MeOH in DCM to give 0.50 g (65% yield) of the titled compound.

Workup

  1. temperaturewas refluxed for 90 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by silica gel column chromatography
  4. washeluted with 2% MeOH in DCM

Sources & evidence

ORD record
ord-c7a2e6ea4fa742208557da471a08eaa9
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Linked notes

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