Dicyclohexylcarbodiimide → tert-butyl 4-((N,2-dimethylpyrazine-3-carboxamido)methyl)thiazol-2-ylcarbamate

HRID 1685026Notes

Reaction equation

HRID 1685026 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[S:7][CH:8]=1.[CH3:17][C:18]1[C:19]([C:24](O)=[O:25])=[N:20][CH:21]=[CH:22][N:23]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH3:1][N:2]([CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[S:7][CH:8]=1)[C:24]([C:19]1[C:18]([CH3:17])=[N:23][CH:22]=[CH:21][N:20]=1)=[O:25]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 131534683-Methylpyrazine-2-carboxylic acidHCID 58055063tert-Butyl (4-((methylamino)methyl)thiazol-2-yl)carbamate2×

Product 1

HCID 86661290tert-butyl 4-((N,2-dimethylpyrazine-3-carboxamido)methyl)thiazol-2-ylcarbamateYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((methylamino)methyl)thiazol-2-ylcarbamate (Intermediate 17, 1.30 g, 5.3 mmol) and 3-methylpyrazine-2-carboxylic acid (1.1 g, 8 mmol) in CH2Cl2 (25 mL) was added DCC (1.64 g, 8 mmol). The mixture was stirred for 2 hours and the solids were removed by filtration. The filtrate was concentrated in vacuo and purified by column chromatography (2% MeOH in CH2Cl2, Rf=0.15) to afford tert-butyl 4-((N,2-dimethylpyrazine-3-carboxamido)methyl)thiazol-2-ylcarbamate (1.30 g, 3.6 mmol) as an off-white solid in 68% yield.

Workup

  1. customthe solids were removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by column chromatography (2% MeOH in CH2Cl2, Rf=0.15)

Sources & evidence

ORD record
ord-6e32e54880294ca7b352c36501677a09
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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