Benzylamine → 2-Amino-4-benzylthiazole-5-carboxylic Acid Benzylamide

HRID 45315Notes

Reaction equation

HRID 45315 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:14]([OH:16])=O)=[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:48]([NH2:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:48]([NH:55][C:14]([C:4]1[S:3][C:2]([NH2:1])=[N:6][C:5]=1[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:16])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 822255112-Amino-4-benzylthiazole-5-carboxylic acid

Product 1

HCID 866425132-Amino-4-benzylthiazole-5-carboxylic Acid BenzylamideYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-4-benzylthiazole-5-carboxylic acid (0.033 g, 0.14 mmol) and diisopropylethylamine (0.08 mL, 0.46 mmol) in N,N-dimethylformamide (5 mL) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.039 g, 0.20 mmol), followed by the addition of 1-hydroxybenzotriazole (0.026 g, 0.19 mmol). After 30 minutes, benzylamine (0.02 mL, 0.18 mmol) was added. The reaction mixture was stirred at ambient temperature for 12 h, diluted with ethyl acetate, washed with water, brine, dried over anhydrous Na2SO4, 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 the title compound (0.029 g, 65% yield).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous Na2SO4
  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-3f803fe591544eb0ae89adf6407e75c4
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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