Hydrochloric Acid → HCID 67073863, compound

HRID 2093745Notes

Reaction equation

HRID 2093745 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[N:20]=[C:19]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[N:18]=[C:17]([NH:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34]C)=[O:33])=[CH:30][CH:29]=2)[N:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[N:20]=[C:19]([O:21][CH2:22][C:23]([F:24])([F:26])[F:25])[N:18]=[C:17]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:36][CH:37]=2)[N:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67074211Methyl 4-(4-(3-(4-(3-aminopropoxy)butoxy)propylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

Product 1

HCID 67073863HCID 67073863, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a suspension of methyl 4-(4-(3-(4-(3-aminopropoxy)butoxy)propylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (0.1 g) in acetone (6 mL) was added potassium carbonate in water (6.00 mL). The mixture was heated to reflux for 16 hours. After cooling to r.t., the reaction solution was acidified with 1N HCl to pH=3. All the solvents were removed under vacuum. The residue was purified by prep. HPLC to give 4-(4-(3-(4-(3-aminopropoxy)butoxy)propylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid (28 mg, 0.054 mmol).

Workup

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

Sources & evidence

ORD record
ord-f8e5df32b3b944709ee156dc5faaf5c9
Source dataset
uspto-grants-2013_05
Patent number
US08445490B2

Reaction notes

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