Benzylamine → HCID 68702539, compound

HRID 45389Notes

Reaction equation

HRID 45389 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:18])[C:9]1[S:10][C:11]([C:15]([OH:17])=O)=[C:12]([CH3:14])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[CH2:43]([NH2:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:43]([NH:50][C:15]([C:11]1[S:10][C:9]([N:8]([CH3:18])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:13][C:12]=1[CH3:14])=[O:17])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 687014412-(Tert-butoxycarbonyl(methyl)amino)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 68702539HCID 68702539, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(tert-butoxycarbonyl(methyl)amino)-4-methylthiazole-5-carboxylic acid (0.070 g, 0.26 mmol) in dichloromethane (2 mL) at 0° C. was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.15 g, 0.39 mmol), followed by the addition of benzylamine (29.5 μL, 0.27 mmol), 4-dimethylaminopyridine (catalytical amount), and triethylamine (72 μL, 0.52 mmol). The reaction mixture was allowed to warm to ambient temperature over 3 h, followed by the addition of saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford tert-butyl 5-(benzylcarbamoyl)-4-methylthiazol-2-yl(methyl)carbamate (0.030 g, 0.083 mmol).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography
  6. washeluting with ethyl acetate/hexanes (5/95 to 100/0)

Sources & evidence

ORD record
ord-d7dbcd892c6749cc8cb9259ca3bae5dd
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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