Hydrogen Bromide → HCID 90120278, compound

HRID 2202550Notes

Reaction equation

HRID 2202550 reaction equation
[I:1][C:2]1[NH:6][C:5]([C@@H:7]([NH:17]C(=O)OCC2C=CC=CC=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:15][CH3:16])=[O:14])=[N:4][CH:3]=1.Br>C(Cl)Cl.CC(O)=O.CO>[NH2:17][C@H:7]([C:5]1[NH:6][C:2]([I:1])=[CH:3][N:4]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:15][CH3:16])=[O:14]

Participants

6

Reactant 2

HCID 260Hydrogen BromideHCID 90149279HCID 90149279, compound

Product 1

HCID 90120278HCID 90120278, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of D6 in DCM (0.2 M) was treated with an excess of HBr solution in AcOH at 0° C. and the reaction mixture was stirred at this temperature for 1 h. Then solvents were removed under reduced pressure and excess reagents were removed by repeated addition of toluene and evaporation of the solvent. The residue obtained was dissolved in MeOH, passed through a SCX resin cartridge and the cartridge washed with MeOH. Then, the cartridge was treated with a 7N solution of NH3 in MeOH and the organic solution was concentrated under reduced pressure to give the title compound as a white powder. MS (ES+) C11H19IN4O: 351 (M+H)+.

Workup

  1. customThen solvents were removed under reduced pressure and excess reagents
  2. customwere removed
  3. additionaddition of toluene and evaporation of the solvent
  4. customThe residue obtained
  5. washthe cartridge washed with MeOH
  6. additionThen, the cartridge was treated with a 7N solution of NH3 in MeOH
  7. concentrationthe organic solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-673265bb3ec24c1e941b550ba87c7b62
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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