Trifluoroacetic acid → HCID 51356287, compound

HRID 2367639Notes

Reaction equation

HRID 2367639 reaction equation
CC(N(C[C@@H:10]1[CH2:15][C@@H:14]([CH3:16])[CH2:13][N:12]([C:17]2[CH:22]=[C:21]([Cl:23])[N:20]=[C:19]([NH2:24])[N:18]=2)[CH2:11]1)C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O.C[CH2:33][N:34](C(C)C)C(C)C.[CH3:41][C:42]([CH3:48])([CH3:47])[CH2:43][C:44](Cl)=[O:45].C([O-])(O)=O.[Na+]>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:24][C:19]1[N:18]=[C:17]([N:12]2[CH2:13][C@H:14]([CH3:16])[CH2:15][C@@H:10]([N:34]([CH3:33])[C:44](=[O:45])[CH2:43][C:42]([CH3:48])([CH3:47])[CH3:41])[CH2:11]2)[CH:22]=[C:21]([Cl:23])[N:20]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 815143,3-Dimethylbutanoyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86659203HCID 86659203, compound

Product 1

HCID 51356287HCID 51356287, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 1,1-dimethylethyl[(3R,5R)-1-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-3-piperidinyl]methylcarbamate (75 mg, 0.211 mmol) in CH2Cl2 (2 mL) was added TFA (2 mL) and the reaction was let sit at room temperature for 2 hours. Toluene (˜15 mL) was added, and the resulting mixture was evaporated under vacuum. To the resulting residue were added CH2Cl2 (2 mL) and Hunig's base (0.18 mL, 1.05 mmol) followed by 3,3-dimethylbutanoyl chloride (0.03 mL, 0.21 mmol), and the resulting mixture was stirred overnight at room temperature. Saturated aqueous NaHCO3 (20 mL) was added, and the resulting mixture was extracted with EtOAc (˜50 mL). The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated to afford the title compound (80 mg). LC-MS (ES) m/z=354 [M+H]+.

Workup

  1. customthe resulting mixture was evaporated under vacuum
  2. extractionthe resulting mixture was extracted with EtOAc (˜50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a04646d0f144489398b884fdd4ca7b79
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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