Hydrochloric Acid → HCID 67073862, compound

HRID 2093748Notes

Reaction equation

HRID 2093748 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[N:19]=[C:18]([NH:28][C:29]3([C:32]([O:34]CC)=[O:33])[CH2:31][CH2:30]3)[N:17]=2)=[CH:11][CH:10]=1)=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([O:22][CH2:23][C:24]([F:25])([F:26])[F:27])[N:19]=[C:18]([NH:28][C:29]3([C:32]([OH:34])=[O:33])[CH2:31][CH2:30]3)[N:17]=2)=[CH:11][CH:10]=1)=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67074087HCID 67074087, compound

Product 1

HCID 67073862HCID 67073862, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Ethyl 1-(4-(4-(4-aminobutylcarbamoyl)phenylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)cyclopropanecarboxylate (80 mg) and potassium carbonate (64.8 mg) were dissolved in acetone (3 mL)/water (2 mL). After stirring at r.t. for 16 hours and then heated to 90° C. for 2 hours, the mixture was acidified with 1N HCl to pH=3. All the solvents were then removed under vacuum. The residue was purified by perp. HPLC to give 1-(4-(4-(4-aminobutylcarbamoyl)phenylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)cyclopropanecarboxylic acid (20 mg).

Workup

  1. temperatureheated to 90° C. for 2 hours
  2. customAll the solvents were then removed under vacuum
  3. customThe residue was purified by perp

Sources & evidence

ORD record
ord-c162c398876a4968b8185472bf4654bf
Source dataset
uspto-grants-2013_05
Patent number
US08445490B2

Reaction notes

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