1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 118113929, compound

HRID 918864Notes

Reaction equation

HRID 918864 reaction equation
OC1C2N=NNC=2C=CC=1.C(N(CC)C(C)C)(C)C.C(N=C=NCCCN(C)C)C.[Br:31][C:32]1[S:36][C:35]2=[N:37][C:38]([C:40]([OH:42])=O)=[CH:39][N:34]2[CH:33]=1.[C:43]([C:47]1[CH:52]=[CH:51][C:50]([CH2:53][NH2:54])=[CH:49][CH:48]=1)([CH3:46])([CH3:45])[CH3:44]>C(Cl)Cl.CN(C)C=O>[Br:31][C:32]1[S:36][C:35]2=[N:37][C:38]([C:40]([NH:54][CH2:53][C:50]3[CH:51]=[CH:52][C:47]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:48][CH:49]=3)=[O:42])=[CH:39][N:34]2[CH:33]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27356554-tert-ButylbenzylamineHCID 127446152-Bromoimidazo[2,1-b]thiazole-6-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 118113929HCID 118113929, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Hydroxybenzotriazole (109 mg, 0.81 mmol), N,N-diisopropylethylamine (0.23 ml, 1.34 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (155 mg, 0.81 mmol) were sequentially added to a the solution of 2-bromoimidazo[2,1-b]thiazole-6-carboxylic acid (supplied by Chemizon, 200 mg, 0.81 mmol) in a solvent mixture of methylene chloride (5 ml) and N,N-dimethyl formamide (2 ml) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. After the addition of (4-(tert-butyl)phenyl)methanamine (0.42 ml, 2.78 mmol) at room temperature, the reaction mixture was stirred at room temperature for 24 hours, then diluted with methylene chloride. The reaction mixture was partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride. The combined organic layer was washed with brine, then dried over anhydrous magnesium sulfate. After concentration, water was added to the residue. Filtration, followed by drying in vacuo, gave the title compound, 2-bromo-N-(4-(tert-butyl)benzyl)imidazo[2,1-b]thiazole-6-carboxamide, as a solid (148 mg, 87% yield).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 24 hours
  2. customThe reaction mixture was partitioned between methylene chloride and water
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationAfter concentration, water
  7. additionwas added to the residue
  8. filtrationFiltration
  9. customby drying in vacuo

Sources & evidence

ORD record
ord-5a27e4f24ec44bed8e3b6562b99daee3
Source dataset
uspto-grants-2016_03
Patent number
US09271969B2

Reaction notes

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