Ethyl Acetate → HCID 71247923, compound

HRID 1055121Notes

Reaction equation

HRID 1055121 reaction equation
[C:1]([N:5]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[NH:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=3)[N:16](S(C3C=CC(C)=CC=3)(=O)=O)[CH:15]=2)[N:8]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>C1COCC1.[Cl-].[Na+].O>[C:1]([N:5]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[NH:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]([F:26])([F:24])[F:25])[CH:21]=3)[NH:16][CH:15]=2)[N:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 71247820HCID 71247820, compound2×

Product 1

HCID 71247923HCID 71247923, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 2-(1-tert-butyl-2-(5-fluoro-2-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)hydrazinyl)ethanoate, 154a, (0.54 g, 0.89 mmol) in THF (20 mL) was added tetrabutylammonium fluoride (1.78 mL of 1 M, 1.78 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted into EtOAc and brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (70% EtOAc/Hexanes) to afford 300 mg of the desired product. 1H NMR (400 MHz, CDCl3) δ 10.59 (s, 1H), 9.55 (s, 1H), 8.66 (s, 1H), 8.29 (d, J=2.2 Hz, 1H), 8.13 (dd, J=3.8, 1.5 Hz, 1H), 7.14 (s, 1H), 4.20-4.04 (m, 2H), 3.85 (s, 2H), 1.28 (d, J=9.1 Hz, 9H), 1.19 (dt, J=7.1, 3.6 Hz, 3H). LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.93 min, (M+H) 455.43.

Workup

  1. dry with materialThe organic phase was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified via silica gel chromatography (70% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-ef31fc7d7975406ea87e82170a4caa13
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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