Trifluoroacetic acid → HCID 86717788, compound

HRID 1468838Notes

Reaction equation

HRID 1468838 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:31]=[CH:32][C:33]=1[C:34]([N:36]([O:38][CH3:39])[CH3:37])=[O:35])[CH2:12][O:13][CH2:14][C@@H:15]1[CH2:17][C@@H:16]1[CH:18]1[CH2:23][CH2:22][N:21]([C:24](OC(C)(C)C)=O)[CH2:20][CH2:19]1.C([O-])([O-])=O.[Cs+].[Cs+].ClC1[N:52]=[CH:51][C:50]([Cl:53])=[CH:49][N:48]=1>C(Cl)Cl.O>[Cl:53][C:50]1[CH:49]=[N:48][C:24]([N:21]2[CH2:20][CH2:19][CH:18]([C@H:16]3[CH2:17][C@H:15]3[CH2:14][O:13][CH2:12][C:11]3[CH:31]=[CH:32][C:33]([C:34]([N:36]([O:38][CH3:39])[CH3:37])=[O:35])=[C:9]([F:8])[CH:10]=3)[CH2:23][CH2:22]2)=[N:52][CH:51]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 5906412,5-DichloropyrimidineHCID 86717789HCID 86717789, compound

Product 1

HCID 86717788HCID 86717788, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of product from step B (35 mg, 0.078 mmol) in DCM (1 mL) and the resulting mixture stirred at RT for 15 min. The mixture was evaporated and the residue dissolved in DMF (1 mL) and Cs2CO3 (76 mg, 0.233 mmol) and 2,5-dichloropyrimidine (13.89 mg, 0.093 mmol) added. The resultant mixture was stirred at RT overnight, diluted with water and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent EtOAc/hexanes 0-100%) to yield the title compound. 1H NMR (500 MHz, CDCl3) δ 8.02 (s, 1H), 7.44 (m, 1H), 7.17 (d, 1H), 7.13 (d, 1H), 4.72-4.62 (m, 2H), 4.61 (d, 1H), 4.55 (d, 1H), 3.66-3.53 (m, 4H), 3.53-3.47 (m, 1H), 3.38 (br s, 3H), 2.89-2.81 (m, 2H), 1.97 (d, 1H), 1.93 (d, 1H), 1.43-1.31 (m, 2H), 1.29-1.20 (m, 1H), 1.11-1.02 (m, 1H), 0.81-0.69 (m, 2H), 0.09-0.04 (m, 1H). MS (ESI) m/z 463 [M+H]+.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue dissolved in DMF (1 mL)
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (eluent EtOAc/hexanes 0-100%)

Sources & evidence

ORD record
ord-178093e4cf25426199c639582fbd6ab0
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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