Benzylamine → 2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

HRID 1879220Notes

Reaction equation

HRID 1879220 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH2:11]([NH:18][C:8]([C:4]1[S:3][C:2]([Br:1])=[N:6][C:5]=1[CH3:7])=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 28240582-Bromo-4-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamideYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid (3.00 g, 13.51 mmol) in methylene chloride (20 mL) was added benzyl amine (1.60 mL, 14.86 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (6.57 g, 14.86 mmol) and N,N-diisopropylethylamine (4.71 mL, 27.02 mmol) and the mixture was stirred under nitrogen at room temperature for 16 hr. The reaction mixture was diluted with methylene chloride (100 mL), and washed with water (100 mL) and brine (2×100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash-chromatography (eluent hexanes-ethyl acetate, 1:1) to provide 2-bromo-4-methyl-thiazole-5-carboxylic acid benzyl amide as a yellow solid (3.50 g, 83% yield). MS (M+H)+=312; Rt=1.31 min.

Workup

  1. washwashed with water (100 mL) and brine (2×100 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by flash-chromatography (eluent hexanes-ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-8f29375dc00b47739c6f9f16adb3167c
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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