2-[6-nitrobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide → 2-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

HRID 1091674Notes

Reaction equation

HRID 1091674 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]2[NH:8][C:9](=[C:11]([C:15]3[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][N:16]=3)[C:12]([NH2:14])=[O:13])[S:10][C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:26]=[CH:25][C:7]2[NH:8][C:9](=[C:11]([C:15]3[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][N:16]=3)[C:12]([NH2:14])=[O:13])[S:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 665934342-[6-nitrobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

Product 1

HCID 665937372-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Compound 32A was prepared from compound 26A as follows. To a solution of 2-[6-nitrobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (280 mg, 0.73 mmol) in MeOH (25 mL) was added a slurry of 10% palladium on carbon (200 mg) in MeOH (10 mL), and the mixture was stirred under hydrogen at atmospheric pressure for 24 hr. The mixture was filtered and the filtrate concentrated to give crude 2-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide as a red powder. This was purified by flash column chromatography eluting with 19:1 EA/MeOH to give pure 2-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide, compound 32A (160 mg, 62% yield) as a yellow powder.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-fe21c686f00942b7a3de06eb0ee92350
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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