Hydrogen Bromide → HCID 86651033, compound

HRID 1890424Notes

Reaction equation

HRID 1890424 reaction equation
C(OC([N:6]1[CH2:12][CH:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]2=[N:21][C:22]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][N:27]=3)=[CH:23][C:24](=[O:25])[N:9]2[CH2:8][CH2:7]1)=O)C.[BrH:32]>C(O)(=O)C>[BrH:32].[CH2:14]([NH:13][CH:11]1[C:10]2=[N:21][C:22]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][N:27]=3)=[CH:23][C:24](=[O:25])[N:9]2[CH2:8][CH2:7][NH:6][CH2:12]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 44178075HCID 44178075, compound

Product 1

HCID 86651033HCID 86651033, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.090 g (0.21 mmol) of 9-benzylamino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester dissolved in 3.00 mL of glacial acetic acid was added 0.75 mL (4.28 mmol) of hydrobromic acid (33 wt % solution in glacial acetic acid). The resulting mixture was stirred at 80° C. for 16 hours, cooled and evaporated to dryness. Toluene was added to the residue and evaporated. Ethanol was added to the residue and evaporated. The crude was triturated with diethyl ether and dichloromethane and filtered to afford 0.083 g (76%) of the product as a powder.

Workup

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

Sources & evidence

ORD record
ord-d8a76b89f9e049a0bf9045d6cf5bb8ef
Source dataset
uspto-grants-2013_08
Patent number
US08507476B2

Reaction notes

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