Hydrogen Bromide → (+/-)-9-Ethyl-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-5H-1,4-a,7-triaza-benzocyclohepten-4-one hydrobromide

HRID 1520427Notes

Reaction equation

HRID 1520427 reaction equation
C(OC([N:6]1[CH2:12][CH:11]([CH2:13][CH3:14])[C:10]2=[N:15][C:16]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][N:21]=3)=[CH:17][C:18](=[O:19])[N:9]2[CH2:8][CH2:7]1)=O)C.[BrH:26]>C(O)(=O)C>[BrH:26].[CH2:13]([CH:11]1[C:10]2=[N:15][C:16]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][N:21]=3)=[CH:17][C:18](=[O:19])[N:9]2[CH2:8][CH2:7][NH:6][CH2:12]1)[CH3:14]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 44598875(+/-)-9-Ethyl-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4-a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester

Product 1

HCID 68832028(+/-)-9-Ethyl-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-5H-1,4-a,7-triaza-benzocyclohepten-4-one hydrobromideYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 0.075 g (0.22 mmol) of (+/−)-9-ethyl-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4-a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester (example 10) dissolved in 0.8 mL of glacial acetic acid was added 0.77 mL (4.37 mmol) of hydrobromic acid (33 wt % solution in glacial acetic acid). The resulting mixture was stirred at 90° C. for 4 hours, cooled and evaporated to dryness. Methanol was added to the residue and evaporated. Toluene was added to the residue and evaporated. The crude was triturated with diethyl ether and filtered to afford 0.068 g of the product as a white powder (88%).

Workup

  1. temperaturecooled
  2. customevaporated to dryness
  3. additionMethanol was added to the residue
  4. customevaporated
  5. additionToluene was added to the residue
  6. customevaporated
  7. customThe crude was triturated with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-d8dc65b278154197b8251110e2ed481d
Source dataset
uspto-grants-2015_07
Patent number
US09073914B2

Reaction notes

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