Trifluoroacetic acid → HCID 86679702, compound

HRID 2367708Notes

Reaction equation

HRID 2367708 reaction equation
C(O)(C(F)(F)F)=O.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=3)[N:19](C3CCCCO3)[N:18]=2)=[O:16])[CH:9]=1.C([SiH](CC)CC)C>C(Cl)Cl>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=3)[NH:19][N:18]=2)=[O:16])[CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052TriethylsilaneHCID 86679703HCID 86679703, compound

Product 1

HCID 86679702HCID 86679702, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5.0 mL) was added to a solution of N,5-di(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxamide (CXXXIV) (0.36 g, 0.90 mmol) and triethylsilane (0.29 mL, 1.81 mmol) in DCM (5.0 mL) The solution was stirred overnight at room temperature. An additional 5.0 mL of TFA was added, and the solution was again stirred overnight. The solvents were removed, and the residue was treated with 7 N ammonia in MeOH. The solvents were again removed, and the product was purified by flash chromatography using a 12 g Thomson normal phase silica gel cartridge (100% CHCl3→5:95 MeOH[7N NH3]:CHCl3) to afford N,5-di(pyridin-3-yl)-1H-indazole-3-carboxamide (4) (0.23 g, 0.73 mmol, 82% yield) as a white solid. 1H NMR (DMSO-d6) δ ppm 14.00 (s, 1H), 10.69 (s, 1H), 9.08 (d, J=2.0 Hz, 1H), 8.93 (d, J=2.0 Hz, 1H), 8.60 (dd, J=4.8, 1.3 Hz, 1H), 8.48-8.47 (m, 1H), 8.33-8.31 (m, 2H), 8.15-8.12 (m, 1H), 7.85-7.81 (m, 2H), 7.54-7.51 (m, 1H), 7.41-7.39 (m, 1H); ESIMS found for C18H13N5O m/z 316 (M+H).

Workup

  1. waitthe solution was again stirred overnight
  2. customThe solvents were removed
  3. additionthe residue was treated with 7 N ammonia in MeOH
  4. customThe solvents were again removed
  5. customthe product was purified by flash chromatography

Sources & evidence

ORD record
ord-4c231d6fd38c4beaaf0ab2178bd2cde0
Source dataset
uspto-grants-2014_04
Patent number
US08697887B2

Reaction notes

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