Triethylamine → 2-{6-[(tert-butyloxycarbonylamino)acetylamino]benzothiazol-2(3H)-ylidene}-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

HRID 1091675Notes

Reaction equation

HRID 1091675 reaction equation
Cl.[C:2]([O:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])([CH3:5])([CH3:4])[CH3:3].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:45][C:46]1[CH:68]=[CH:67][C:49]2[NH:50][C:51](=[C:53]([C:57]3[N:62]=[C:61]([C:63]([F:66])([F:65])[F:64])[CH:60]=[CH:59][N:58]=3)[C:54]([NH2:56])=[O:55])[S:52][C:48]=2[CH:47]=1>CN(C=O)C.CC(=O)OCC>[C:2]([O:6][C:7]([NH:9][CH2:10][C:11]([NH:45][C:46]1[CH:68]=[CH:67][C:49]2[NH:50][C:51](=[C:53]([C:57]3[N:62]=[C:61]([C:63]([F:66])([F:65])[F:64])[CH:60]=[CH:59][N:58]=3)[C:54]([NH2:56])=[O:55])[S:52][C:48]=2[CH:47]=1)=[O:13])=[O:8])([CH3:3])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19004789N-Boc-glycine hydrochlorideHCID 665937372-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

Product 1

HCID 665933642-{6-[(tert-butyloxycarbonylamino)acetylamino]benzothiazol-2(3H)-ylidene}-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 76A was prepared from compound 32A as follows. To a solution of N-(tert-butoxycarbonyl)glycine hydrochloride (20 mg) in DMF (5 mL) were added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (190 mg), triethylamine (388 μL, 3.88 mmol), and 2-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (141 mg). The mixture was stirred at room temperature for 1 hr, then poured into EA (50 mL). The EA layer was washed three times with 10% aqueous sodium bicarbonate (30 mL each), and three times with water (15 mL each), then dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 2-{6-[(tert-butyloxycarbonylamino)acetylamino]benzothiazol-2(3H)-ylidene}-2-(4-trifluoromethylpyrimidin-2-yl)acetamide as a brown foam. 2-{6-[(Tert-butyloxycarbonylamino)-acetylamino]benzothiazol-2(3H)-ylidene}-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (80 mg, 156 mmol) was dissolved in 4N hydrogen chloride in dioxane (5.0 mL, 20 mmol), and the mixture stirred at room temperature for 2 hr. The mixture was concentrated to give 2-{6-[(2-aminoacetyl)-amino]benzothiazol-2(3H)-ylidene}-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (50 mg) as a beige solid. Other compounds with an amide side-chain may be similarly prepared from compound 32A.

Workup

  1. washThe EA layer was washed three times with 10% aqueous sodium bicarbonate (30 mL each), and three times with water (15 mL each)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f8e598414ca4fe694d5c9560153dfeb
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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