Diisopropylethylamine → Tert-butyl 5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-ylcarbamate

HRID 1188136Notes

Reaction equation

HRID 1188136 reaction equation
[I-].ClC1C=CC=C[N+]=1C.CCN(C(C)C)C(C)C.[C:19]1([CH3:31])[CH:24]=[CH:23][C:22]([C:25]2[N:26]=[C:27]([NH2:30])[S:28][CH:29]=2)=[CH:21][CH:20]=1.[C:32]([O:36][C:37]([NH:39][C:40]1[S:41][C:42]([C:45](O)=[O:46])=[CH:43][N:44]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33]>CN(C=O)C.CCOC(C)=O>[C:19]1([CH3:31])[CH:20]=[CH:21][C:22]([C:25]2[N:26]=[C:27]([NH:30][C:45]([C:42]3[S:41][C:40]([NH:39][C:37](=[O:38])[O:36][C:32]([CH3:34])([CH3:33])[CH3:35])=[N:44][CH:43]=3)=[O:46])[S:28][CH:29]=2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 2440664-(4-Methylphenyl)-1,3-thiazol-2(3H)-imineHCID 222714422-N-Boc-Amino-Thiazole-5-Carboxylic Acid

Product 1

HCID 86643475Tert-butyl 5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-ylcarbamateYield 17%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-methylpyridinium iodide (0.47 g, 1.84 mmol), DIEA (0.44 mL, 2.5 mmol) and 4-p-tolylthiazol-2-amine (0.24 g, 1.23 mmol) were added to a solution of 2-(tert-butoxycarbonylamino)thiazole-5-carboxylic acid (0.30 g, 1.23 mmol) in DMF (5 mL). The resulting solution was stirred at RT until completion of the reaction. Then the reaction mixture was diluted with AcOEt, washed with water, dried with Na2SO4 and concentrated. The crude product was purified by column (100% AcOEt), yielding tert-butyl 5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-ylcarbamate (80 mg, 17%) as a solid.

Workup

  1. washwashed with water
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column (100% AcOEt)

Sources & evidence

ORD record
ord-2155fc60129447a88b026887a534213b
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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