Hydrochloric Acid → HCID 67074608, compound

HRID 2042680Notes

Reaction equation

HRID 2042680 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[N:11]=[C:10]([NH:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=2)[N:9]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([O:14][CH2:15][C:16]([F:18])([F:19])[F:17])[N:11]=[C:10]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=2)[N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67074151HCID 67074151, compound

Product 1

HCID 67074608HCID 67074608, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a suspension of methyl 4-(4-(2-(2-aminoethylamino)ethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (0.1 g) in acetone (6 mL) was added potassium carbonate (0.080 g) in water (6.00 mL). The mixture was heated to reflux for 16 hours. After cooling to room temperature, the reaction solution was acidified with 1N HCl to pH=3. All solvents were removed under vacuum. The residue was purified by prep. HPLC to give 4-(4-(2-(2-aminoethylamino)ethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid (40 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. customAll solvents were removed under vacuum
  4. customThe residue was purified by prep

Sources & evidence

ORD record
ord-b3dce74aff7449a3a48ae281a15425c4
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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