Trifluoroacetic acid → HCID 68813644, compound

HRID 2105217Notes

Reaction equation

HRID 2105217 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH:22]3[C:26]3[O:30][N:29]=[C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[CH:27]=3)[N:18]=[C:17]([NH:37][C:38]3[CH:42]=[C:41]([CH3:43])[NH:40][N:39]=3)[CH:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[N:20]=[C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH:22]3[C:26]3[O:30][N:29]=[C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[CH:27]=3)[N:18]=[C:17]([NH:37][C:38]3[CH:42]=[C:41]([CH3:43])[NH:40][N:39]=3)[CH:16]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68816915HCID 68816915, compound

Product 1

HCID 68813644HCID 68813644, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(4-(N-tert-Butoxycarbonylamino)piperidin-1-yl)-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Example 124) (120 mg, 0.20 mmol) was stirred in DCM (10 ml) and trifluoroacetic acid (2 ml) was added and the mixture stirred at room temperature for 3 hours. The mixture was concentrated by evaporation and the residue dissolved in methanol (10 ml) and passed down a 20 g SCX-2 ion exchange column, eluting with methanol to elute impurities and then 2M methanolic ammonia to elute the product. The solvent was removed by evaporation to give the title compound (79 mg, 81%) as a cream powder.

Workup

  1. concentrationThe mixture was concentrated by evaporation
  2. dissolutionthe residue dissolved in methanol (10 ml)
  3. washeluting with methanol
  4. washto elute impurities
  5. wash2M methanolic ammonia to elute the product
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-b89c4ccf4c4a4bcc8234e278d2be7437
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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