Lawesson's reagent → 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-thiobenzamide

HRID 737170Notes

Reaction equation

HRID 737170 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:18]=[CH:17][C:10]([C:11]([NH:13][CH:14]3[CH2:16][CH2:15]3)=O)=[CH:9][CH:8]=2)[N:6]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1COCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:18]=[CH:17][C:10]([C:11]([NH:13][CH:14]3[CH2:16][CH2:15]3)=[S:28])=[CH:9][CH:8]=2)[N:6]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 592287924-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide

Product 1

HCID 866164304-(2-Amino-thiazol-4-yl)-N-cyclopropyl-thiobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide (265 mg, 1 mmol), in THF (5 mL), was treated with Lawesson's reagent (0.75 eq) and heated to 70° C. overnight in a sealed vial. The reaction was cooled, filtered and the solvents removed. The resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. MS: 275.4 (M+H+).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customthe solvents removed
  4. dissolutionThe resulting mixture was redissolved in 5 ml of 90% DMF
  5. custom10% water with 0.1% TFA and purified by reverse phase HPLC
  6. customto give the product

Sources & evidence

ORD record
ord-72c6240b19624ebdaed0b4443e6217d6
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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