Trifluoroacetic acid → HCID 86281678, compound

HRID 510227Notes

Reaction equation

HRID 510227 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[C:14]([F:15])=[C:13]([Cl:16])[CH:12]=[CH:11][C:10]=1[C:17]([N:19]1[CH2:28][CH2:27][C:26]2[C:25]([C:29]3[N:33](C4CCCCO4)[N:32]=[CH:31][CH:30]=3)=[N:24][CH:23]=[N:22][C:21]=2[CH2:20]1)=[O:18].C([SiH](CC)CC)C>C(Cl)Cl>[Cl:8][C:9]1[C:14]([F:15])=[C:13]([Cl:16])[CH:12]=[CH:11][C:10]=1[C:17]([N:19]1[CH2:28][CH2:27][C:26]2[C:25]([C:29]3[NH:33][N:32]=[CH:31][CH:30]=3)=[N:24][CH:23]=[N:22][C:21]=2[CH2:20]1)=[O:18]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 90407502HCID 90407502, compound

Product 1

HCID 86281678HCID 86281678, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.97 mL, 0.24 mmol) was added to a solution of the product of Example 20, step b (116 mg, 0.24 mmol) in DCM (1 mL) containing triethylsilane (0.1 mL, 0.61 mmol). The reaction was stirred for 30 min. The reaction was concentrated in vacuo and then azeotroped 2x with toluene. The residue was purified on SiO2 eluting with EtOAc/Hex to afford the title compound as a white solid (97 mg, 100%). MS (ESI) mass calcd. C17H12Cl2FN5O, 391.04. m/z found 392.0 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.11-8.93 (m, 1H), 7.77-7.67 (m, 1H), 7.48-7.37 (m, 1H), 7.15-7.07 (m, 1H), 6.99-6.90 (m, 1H), 5.14-4.96 (m, 1H), 4.61-4.40 (m, 1H), 4.17-4.11 (m, 1H), 3.67-3.51 (m, 1H), 3.36-3.08 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customazeotroped 2x with toluene
  3. customThe residue was purified on SiO2 eluting with EtOAc/Hex

Sources & evidence

ORD record
ord-8c25154bb1794fb780e0496145692773
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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