Acetic Acid → N-Benzylthiazol-2-amine

HRID 593300Notes

Reaction equation

HRID 593300 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:9]1[CH:13]=[CH:12][N:11]=[C:10]1[NH2:14].C(O)(=O)C>C(Cl)Cl.CO.CC(N(C)C)=O>[CH2:1]([NH:14][C:10]1[S:9][CH:13]=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 21552-Aminothiazole

Product 1

HCID 273599N-Benzylthiazol-2-amine

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21226129Dichloromethane methanolSolvent2×

Conditions

Temperature
65 °C

Procedure

In a 20 mL vial, to a solution of benzaldehyde (40 mg, 0.38 mmol) in DCM/MeOH (1.4 mL) was added a solution of thiazol-2-amine (47 mg, 0.47 mmol) in DMA (1.8 mL). A solution of acetic acid (66 mg, 1.1 mmol) in DCM/MeOH (1.4 mL) was then added, followed by the addition of 470 mg of MP-CNBH3 resin (3 eq.; subst. 2.36 mmoles/g). The vial was capped and was then heated with shaking overnight at 65° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound.

Workup

  1. customThe vial was capped
  2. temperaturewas then heated
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated to dryness
  5. dissolutionThe residue was dissolved in 1:1 DMSO/MeOH
  6. customPurification by reverse phase HPLC (TFA method)

Sources & evidence

ORD record
ord-c459b59a63164496beaf5b7d1868f314
Source dataset
uspto-grants-2016_01
Patent number
US09242933B2

Reaction notes

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