Sodium Bicarbonate → HCID 49863889, compound

HRID 545092Notes

Reaction equation

HRID 545092 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]([F:16])([F:15])[F:14])[C:5]([C:8](=O)[CH:9](O)O)=[N:6][CH:7]=1.[F:17][C:18]([F:35])([F:34])[C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH2:32])[C:27]=2[NH2:33])=[N:23][CH:24]=1.C([O-])(O)=O.[Na+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([F:16])([F:15])[F:14])[C:5]([C:8]2[N:32]=[C:28]3[N:29]=[CH:30][CH:31]=[C:26]([NH:25][C:22]4[CH:21]=[CH:20][C:19]([C:18]([F:35])([F:34])[F:17])=[CH:24][N:23]=4)[C:27]3=[N:33][CH:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 67189158HCID 67189158, compoundHCID 86238174HCID 86238174, compound

Product 1

HCID 49863889HCID 49863889, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve the crude 1-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)-2,2-dihydroxyethanone (800 mg, step 3) in 16.0 mL of EtOH, and then add N4-(5-(trifluoromethyl)pyridin-2-yl)pyridine-2,3,4-triamine (162 mg, step 5) followed by NaHCO3 (336 mg). Stir the reaction at room temperature for 18 hours under N2 atmosphere. Concentrate the reaction mixture under vacuum, and purify by column chromatography to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-D6) δ 9.405 (s, 1H), 9.287 (s, 1H), 9.127 (s, 1H), 9.109 (d, 1H, J=1.8 Hz), 8.905 (d, 1H, J=1.8 Hz), 8.728 (s, 1H), 8.380 (s, 1H), 7.883 (dd, 1H, J=0.7 Hz), 7.126(d, 1H, J=2.8 Hz). MS=516.85 (M+H). The IC50 determined as described in Example 6 is less than 1 micromolar.

Workup

  1. customthe reaction at room temperature for 18 hours under N2 atmosphere
  2. concentrationConcentrate the reaction mixture under vacuum
  3. custompurify by column chromatography

Sources & evidence

ORD record
ord-afadf687bdc142d981bf40fe77ba8469
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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