Trifluoroacetic acid → HCID 58513259, compound

HRID 1405057Notes

Reaction equation

HRID 1405057 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C: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[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 58513533HCID 58513533, compound

Product 1

HCID 58513259HCID 58513259, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

630 mg (1.5 mmol) of 4-[2-amino-5-(6-amino-pyridin-3-ylethynyl)-6-methyl-pyrimidin-4-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester are dissolved in DCM (40 mL) and 2 mL TFA are added. The reaction mixture is stirred for 3 h, concentrated aqueous Na2CO3 solution is added until pH 7 is reached and DCM is evaporated at reduced pressure. The residue is washed with water, taken up in acetonitrile and freeze dried yielding 253 mg (0.83 mmol) of the desired product which is used for the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-ced320f41d914d37af9dcc54f914eacc
Source dataset
uspto-grants-2014_12
Patent number
US08916548B2

Reaction notes

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