Acetic Acid Mixture with Hydrobromic Acid → Hydrogen Bromide

HRID 545100Notes

Reaction equation

HRID 545100 reaction equation
C([O:3][C:4]1[N:9]=[N:8][C:7]([C:10]2[N:19]=[C:18]3[C:13]([C:14]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][N:22]=4)=[CH:15][CH:16]=[N:17]3)=[CH:12][CH:11]=2)=[C:6]([C:31]([F:34])([F:33])[F:32])[CH:5]=1)C.[BrH:35].CC(O)=O>>[F:34][C:31]([F:32])([F:33])[C:6]1[CH:5]=[C:4]([OH:3])[N:9]=[N:8][C:7]=1[C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[N:17][CH:16]=[CH:15][C:14]=2[NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][N:22]=2)[N:19]=1.[BrH:35]

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86605108HCID 86605108, compound

Product 2

HCID 260Hydrogen BromideYield 100%HCID 178516127HCID 178516127, compound

Procedure

Dissolve 7-[6-ethoxy-4-(trifluoromethyl)pyridazin-3-yl]-N-[5-(trifluoromethyl)pyridin-2-yl]-1,8-naphthyridin-4-amine (560 mg, 1.16 mmol) in HBr/AcOH (33% wt; 10 mL) and stir for 4 hours at room temperature. Remove the solvent under reduced pressure. Add toluene (25 mL) and remove the solvent under reduced pressure. Dry under vacuum to yield the title compound as its HBr salt (618 mg, 100%). LC/MS (MH+) 453.97.

Workup

  1. customRemove the solvent under reduced pressure
  2. customAdd toluene (25 mL) and remove the solvent under reduced pressure
  3. customDry under vacuum

Sources & evidence

ORD record
ord-3ef3cb50ac8d460482ec319b847fc256
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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