Trifluoroacetic acid → HCID 59705004, compound

HRID 605867Notes

Reaction equation

HRID 605867 reaction equation
C(O)(C(F)(F)F)=O.[N+:8]([C:11]1[C:12]([NH:37][CH:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[N:13][C:14]([NH:17][C:18]2[CH:23]=[C:22]([O:24][C:25]([F:28])([F:27])[F:26])[CH:21]=[CH:20][C:19]=2[NH:29][C:30](=O)OC(C)(C)C)=[N:15][CH:16]=1)([O-:10])=[O:9]>C(Cl)Cl>[N+:8]([C:11]1[C:12]([NH:37][CH:38]2[CH2:39][CH2:40][O:41][CH2:42][CH2:43]2)=[N:13][C:14]([N:17]2[C:18]3[CH:23]=[C:22]([O:24][C:25]([F:28])([F:26])[F:27])[CH:21]=[CH:20][C:19]=3[N:29]=[CH:30]2)=[N:15][CH:16]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59705045HCID 59705045, compound

Product 1

HCID 59705004HCID 59705004, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A freshly prepared solution of 30% TFA in DCM (25 mL) was added to the 1.0 g tert-Butyl 2-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)-4-(trifluoromethoxy)phenylcarbamate and the solution were stirred at room temperature for 2 hrs. The solvents were removed in vacuo to yield an orange residue that was carried on without further purification (MH+=415). This residue was dissolved in 20 mL 1:1 trimethyl orthoformate: MeOH and the resulting solution were stirred for 30 minutes at room temperature. Yellow solids were precipitated from the orange solution. Desired product (0.6 g, 70% overall yield) was obtained after filtration.

Workup

  1. customThe solvents were removed in vacuo
  2. customto yield an orange residue that
  3. customwas carried on without further purification (MH+=415)
  4. dissolutionThis residue was dissolved in 20 mL 1:1 trimethyl orthoformate
  5. stirringMeOH and the resulting solution were stirred for 30 minutes at room temperature
  6. customYellow solids were precipitated from the orange solution

Sources & evidence

ORD record
ord-0f73b3b1b3154849a4dee4a0e6c134bd
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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