Dimethylamine → (4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 32847Notes

Reaction equation

HRID 32847 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][NH:18][CH3:19].O1CCCC1>S(Cl)(Cl)=O.CO>[CH3:17][N:18]([CH3:19])[C:14]([C:12]1[N:13]=[C:9]([NH2:8])[S:10][CH:11]=1)=[O:16].[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[N:18]([CH3:19])[CH3:17])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protected

Product 2

HCID 545942972-amino-N,N-dimethyl-1,3-thiazole-4-carboxamideHCID 86603401(4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl esterYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

2-Amino-thiazole-4-carboxylic acid dimethylamide was prepared as follows. (1) A solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (0.5 g, 2 mmol) (prepared as described in Examples 4a and 4b) in thionyl chloride (10 mL) was heated at reflux (80° C.) for 2 hours. The reaction mixture was then concentrated under reduced pressure. To the residue was added a 2 M solution of dimethylamine in tetrahydrofuran (10 mL, 20 mmol) and methanol (10 mL). The reaction mixture was stirred at room temperature for 20 hours and concentrated. The residue was purified by chromatography over silica gel eluted with 2:1 ethyl acetate/hexanes to give (4-dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester as a yellow foam (0.26 g, 48%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography over silica gel
  4. washeluted with 2:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fee1464fa8e24b5288cdc61705cefdd9
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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