Trifluoroacetic acid → HCID 58513370, compound

HRID 1405053Notes

Reaction equation

HRID 1405053 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]#[C:21][C:22]3[CH:23]=[N:24][C:25]([NH2:28])=[CH:26][CH:27]=3)=[C:18]([CH3:29])[N:17]=[C:16]([NH2:30])[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:28][C:25]1[N:24]=[CH:23][C:22]([C:21]#[C:20][C:19]2[C:18]([CH3:29])=[N:17][C:16]([NH2:30])=[N:15][C:14]=2[N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 58513135HCID 58513135, compound

Product 1

HCID 58513370HCID 58513370, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.1 g (17.3 mmol) of 4-[2-amino-5-(6-amino-pyridin-3-ylethynyl)-6-methyl-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester are dissolved in DCM (400 mL) and 40 mL TFA are added. The reaction mixture is stirred over night at RT. The reaction mixture is adjusted to neutral pH using concentrated aqueous Na2CO3 solution and the DCM is evaporated at reduced pressure. The residue is washed with water, taken up in acetonitrile and freeze dried yielding 4.0 g (13.0 mmol) of the desired product which is used for the next step without further purification.

Workup

  1. customthe DCM is evaporated at reduced pressure
  2. washThe residue is washed with water
  3. customfreeze dried

Sources & evidence

ORD record
ord-96233080cb574457abfd241b93c9fd98
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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