Trifluoroacetic acid → HCID 86713599, compound

HRID 2404065Notes

Reaction equation

HRID 2404065 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[C:5]([Cl:21])=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O.ClC1N=C(N2CCNCC2)C(Cl)=CN=1.[C:43]([O:47][C:48](=[O:57])[NH:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[NH2:56])([CH3:46])([CH3:45])[CH3:44]>C(Cl)Cl.O1CCOCC1.CCOC(C)=O>[C:43]([O:47][C:48](=[O:57])[NH:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[NH:56][C:2]1[N:7]=[C:6]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[C:5]([Cl:21])=[CH:4][N:3]=1)([CH3:46])([CH3:44])[CH3:45]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 79631890HCID 79631890, compoundHCID 86713598HCID 86713598, compound

Product 1

HCID 86713599HCID 86713599, compoundYield 23.1%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(2,5-dichloropyrimidin-4-yl)piperazine-1-carboxylate (0.1 g, 0.3 mmol) in DCM (1.0 mL) was added TFA (1.0 mL) and the mixture was stirred for 1 h. An aliquot of the reaction mixture was analyzed by LCMS, which indicated that the reaction had proceeded to completion. The solvents were removed and the residue was dried on high vacuum. The crude product was used for the next step without further purification. To a solution of 2,5-dichloro-4-(piperazin-1-yl)pyrimidine (0.3 mmol) in Dioxane (4.0 mL) was added TFA (0.060 mL, 0.75 mmol) and tert-butyl(2-aminophenyl)carbamate (0.094 g, 0.45 mmol) and the mixture was stirred at 100° C. for 24 h. reaction. After cooling to room temperature the reaction mixture was diluted with EtOAc and washed with aqueous saturated sodium bicarbonate solution. The organic mixture was dried over sodium sulfate and loaded onto silica gel and purified using 0-10% MeOH/DCM gradient containing 10% NH4OH to give the title compound (28 mg, 23%) as a white solid. MS (ES+) C19H25ClN6O2 requires: 404. found: 405 [M+H]+

Workup

  1. customThe solvents were removed
  2. customthe residue was dried on high vacuum
  3. customThe crude product was used for the next step without further purification
  4. stirringthe mixture was stirred at 100° C. for 24 h.
  5. customreaction
  6. washwashed with aqueous saturated sodium bicarbonate solution
  7. dry with materialThe organic mixture was dried over sodium sulfate
  8. custompurified
  9. additioncontaining 10% NH4OH

Sources & evidence

ORD record
ord-620eb353c2b24df4a9ec4e939a8027be
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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