Trifluoroacetic acid → HCID 57537665, compound

HRID 1693710Notes

Reaction equation

HRID 1693710 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:18]=2)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:6][N:5]=[C:4]2[N:19](COCC[Si](C)(C)C)[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:3]=12.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:18]=2)[C:13]([N:15]([CH3:16])[CH3:17])=[O:14])=[CH:6][N:5]=[C:4]2[NH:19][CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:3]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57537614HCID 57537614, compound

Product 1

HCID 57537665HCID 57537665, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[4-chloro-3-(2-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide was taken up in dichloromethane and 500 μL of trifluoroacetic acid added. The mixture was left at ambient temperature for 10 h and then evaporated. The residue was re-dissolved in 3 mL of dichloromethane and 100 μL of 1,2-ethylenediamine. After 6 h at ambient temperature the mixture was evaporated to dryness. The resulting crude was dissolved in dimethylsulfoxide and purified by mass-triggered reverse phase HPLC to afford 18.2 mg (46 μmol, 33%) of 5-[4-chloro-3-(2-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide as an off-white solid. 1H-NMR [500 MHz, d6-DMSO] δ: 12.50 (s, br., 1H), 8.73 (d, 1H), 8.65 (d, 1H), 8.32 (s, 1H), 7.97 (t, 1H), 7.76 (s, 1H), 7.47 (ddd, 1H), 7.41 (, 1H), 7.28-7.21 (m, 2H), 3.01 (s, 3H), 2.97 (s, 3H); MS [MH+] m/z: 395.

Workup

  1. customevaporated
  2. dissolutionThe residue was re-dissolved in 3 mL of dichloromethane
  3. customAfter 6 h at ambient temperature the mixture was evaporated to dryness
  4. dissolutionThe resulting crude was dissolved in dimethylsulfoxide
  5. custompurified by mass-triggered reverse phase HPLC

Sources & evidence

ORD record
ord-c0f802bba7a44cfeb90347ed41530ca4
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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