Trifluoroacetic acid → HCID 22594114, compound

HRID 1760969Notes

Reaction equation

HRID 1760969 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[N:27]=[C:26]([NH:28][C:29]3[CH:34]=[C:33]([NH:35][C:36]([C:38]4[CH:43]=[CH:42][N:41]=[C:40]([N:44]5[CH2:49][CH2:48][O:47][CH2:46][CH2:45]5)[CH:39]=4)=[O:37])[CH:32]=[CH:31][C:30]=3[CH3:50])[CH:25]=[CH:24][N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH3:50][C:30]1[CH:31]=[CH:32][C:33]([NH:35][C:36]([C:38]2[CH:43]=[CH:42][N:41]=[C:40]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[CH:39]=2)=[O:37])=[CH:34][C:29]=1[NH:28][C:26]1[CH:25]=[CH:24][N:23]=[C:22]([O:21][CH:18]2[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)[N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22594083HCID 22594083, compound

Product 1

HCID 22594114HCID 22594114, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to a solution of 2(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)anilino]pyrimidine (0.212 g) in methylene chloride (5 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and water. The aqueous phase was passed through an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Hengoed, Mid-Glamorgan, UK) using a 99:1 mixture of methanol and a saturated aqueous ammonium hydroxide solution as eluent. The product so obtained was triturated under diethyl ether and there was thus obtained the title compound as a solid (0.065 g); NMR Spectrum: (DMSOd6) 1.2 (m, 2H), 1.87 (m, 2H), 2.17 (s, 3H), 2.19 (s, 3H), 2.27 (m, 2H), 2.95 (m, 2H), 3.5 (m, 4H), 3.7 (m, 4H), 4.85 (m, 1H), 6.27 (d, 1H), 7.1 (m, 1H), 7.21 (s, 1H), 7.23 (m, 1H), 7.5 (m, 1H), 7.9 (m, 1H), 8.0 (d, 1H), 8.27 (m, 1H), 9.0 (s, 1H), 10.28 (s, 1H); Mass Spectrum: M+H+ 490.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride and water
  3. additiona 99:1 mixture of methanol
  4. customThe product so obtained
  5. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-ac1f8de58186481a8baae5e0d66e4a70
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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