4,5-dihydro-1H-imidazol-2-ylamine tosylate → 2-amino-5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)benzamide

HRID 1631543Notes

Reaction equation

HRID 1631543 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH:12]1[CH2:16][CH2:15][N:14]=[C:13]1[NH2:17].[Na].C(NC(C=C([C:29]1[C:30]([NH2:39])=[C:31]([CH:35]=[C:36]([Br:38])[CH:37]=1)[C:32]([O-])=[O:33])C)=O)(C)(C)C>CC(O)C>[NH2:39][C:30]1[CH:29]=[CH:37][C:36]([Br:38])=[CH:35][C:31]=1[C:32]([NH:17][C:13]1[NH:14][CH2:15][CH2:16][N:12]=1)=[O:33]

Participants

5

Reactant 3

HCID 2865314,5-dihydro-1H-imidazol-2-ylamine tosylateHCID 5360545SodiumHCID 867104611-(tert-Butylcarbamoyl)-prop-1-en-2-yl-2-amino-5-bromobenzoate

Product 1

HCID 715549862-amino-5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4,5-dihydro-1H-imidazol-2-ylamine tosylate (0.523 g; 2.03 mmol) and sodium (37 mg; 1.63 mmol) in 2-propanol (16 ml) is refluxed for 30 min. 1-(tert-Butylcarbamoyl)-prop-1-en-2-yl-2-amino-5-bromobenzoate (example 15) (0.300 g; 0.812 mmol) is added and the mixture is refluxed over night. The precipitate formed is filtered off and discarded. The filtrate is evaporated, and the residue is purified by preparative RP-HPLC (column: Xbridge C18 (Waters); water-ACN; modifier: ammonia) to yield the title compound (C10H11BrN4O).

Workup

  1. temperatureis refluxed for 30 min
  2. temperaturethe mixture is refluxed over night
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. customThe filtrate is evaporated
  6. customthe residue is purified by preparative RP-HPLC (column: Xbridge C18 (Waters); water-ACN; modifier: ammonia)

Sources & evidence

ORD record
ord-cb7f4741bf524f8fa6c6b016bc815c8e
Source dataset
uspto-grants-2014_07
Patent number
US08791260B2

Reaction notes

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