2-Aminothiazole → HCID 22349608, compound

HRID 896264Notes

Reaction equation

HRID 896264 reaction equation
C([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:5][C:4]=1[N:21]=[CH:22][N:23]([CH3:25])C)#N.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1>C(O)(=O)C>[NH2:26][C:27]1[S:28][C:29]([C:25]2[C:3]3[C:4](=[CH:5][C:6]([O:11][CH2:12][CH2:13][CH2:14][N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)=[C:7]([O:9][CH3:10])[CH:8]=3)[N:21]=[CH:22][N:23]=2)=[CH:30][N:31]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 11595416HCID 11595416, compound

Product 1

HCID 22349608HCID 22349608, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N′-(2-cyano-4-methoxy-5-(3-morpholinopropoxy)phenyl)-N,N-dimethylimidoformamide (692 mg, 2 mmol) was reacted with amino-1,3-thiazole (240 mg, 2.4 mmol) in acetic acid (6.9 ml) at reflux for 4 hours. The mixture was concentrated, the residue dissolved in AcOEt, washed with aqueous sodium bicarbonate, the organic phase was dried, concentrated, the residual oil triturated in ether to give a solid (560 mg, 70%).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue dissolved in AcOEt
  4. washwashed with aqueous sodium bicarbonate
  5. customthe organic phase was dried
  6. concentrationconcentrated
  7. customthe residual oil triturated in ether

Sources & evidence

ORD record
ord-a9bb2746e7a34cbaa352823ca39e1d30
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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