Ethyl Acetate → HCID 68523428, compound

HRID 1437428Notes

Reaction equation

HRID 1437428 reaction equation
[NH2:1][C:2]1[C:3]([NH:15][C@H:16]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:17][OH:18])=[N:4][C:5]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)=[CH:6][CH:7]=1.[C:26](O)(=O)C.C(N)=N.C(=O)(O)[O-].[Na+].CCOC(C)=O>CCO>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C@@H:16]([N:15]2[C:3]3=[N:4][C:5]([NH:8][C:9]4[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=4)=[CH:6][CH:7]=[C:2]3[N:1]=[CH:26]2)[CH2:17][OH:18])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 516892Sodium BicarbonateHCID 68525354HCID 68525354, compound

Product 1

HCID 68523428HCID 68523428, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-2-(3-Amino-6-(5-methyl-1H-pyrazol-3-ylamino)pyridin-2-ylamino)-2-(4-fluorophenyl)ethanol (Method 62, 0.28 g, 0.82 mmol) and formamidine acetate (0.17 g, 1.6 mmol) in EtOH (5 ml) was heated at reflux overnight. Saturated sodium bicarbonate solution (10 ml) and EtOAc (30 ml) was added. The organic layer was separated, washed with brine (10 ml) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by chromatography (EtOAc-MeOH=40:1) to give the title compound as off white solid (0.021 g, 73%). 1H NMR (400 MHz) δ 11.72 (s, 1H), 9.24 (s, 1H), 8.33 (s, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.40 (m, 2H), 7.17 (m, 2H), 6.93 (d, J=8.0 Hz, 1H), 6.27 (s, 1H), 5.71 (br s, 1H), 5.32 (t, J=4.2 Hz, 1H), 4.34 (m, 1H), 4.12 (m, 1H), 4.03 (m, 1H), 2.22 (s, 3H). MS: Calcd.: 352. Found: [M+H]+ 353.

Workup

  1. temperatureat reflux overnight
  2. customThe organic layer was separated
  3. washwashed with brine (10 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by chromatography (EtOAc-MeOH=40:1)

Sources & evidence

ORD record
ord-314e97ecd335486fac24bcdbafb819f8
Source dataset
uspto-grants-2009_11
Patent number
US07622482B2

Reaction notes

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