Ethyl Acetate → HCID 66589124, compound

HRID 1092202Notes

Reaction equation

HRID 1092202 reaction equation
[NH2:1][C:2]1[C:3]([NH:20][C:21]2[CH:25]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[NH:23][N:22]=2)=[CH:4][C:5]([NH:10][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:29](O)(=O)C.C(N)=N.C(=O)(O)[O-].[Na+].CCOC(C)=O>CCO>[CH:26]1([C:24]2[NH:23][N:22]=[C:21]([N:20]3[C:3]4[CH:4]=[C:5]([NH:10][C@H:11]([C:13]5[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=5)[CH3:12])[C:6]([C:7]#[N:8])=[CH:9][C:2]=4[N:1]=[CH:29]3)[CH:25]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 516892Sodium BicarbonateHCID 66589143HCID 66589143, compound

Product 1

HCID 66589124HCID 66589124, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (s)-5-amino-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-[1-(4-fluorophenyl)ethylamino]benzonitrile (Method 69; 3.85 g, 10.2 mmol) and formamidine acetate (2.13 g, 20.5 mmol) in EtOH (50 ml) was heated at reflux for 2 hrs. After cooling, the reaction mixture was treated with saturated sodium bicarbonate solution (10 ml) and EtOAc (30 ml). The organic layer was separated, washed with brine (10 ml), and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (EtOAc:MeOH=30:1) to give the title compound as an off-white solid (3.23 g, 82%). NMR (400 MHz) 12.79 (s, 1H), 8.44 (s, 1H), 7.95 (s, 1H), 7.53 (m, 2H), 7.14 (m, 2H), 7.01 (s, 1H), 6.10 (s, 1H), 6.09 (d, J=7.6 Hz, 1H), 4.63 (m, 1H), 1.97 (m, 1H), 1.55 (d, J=6.8 Hz, 3H), 1.03 (m, 2H), 0.76 (m, 2H). MS: Calcd.: 386; Found: [M+H]+ 387.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hrs
  3. temperatureAfter cooling
  4. customThe organic layer was separated
  5. washwashed with brine (10 ml)
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (EtOAc:MeOH=30:1)

Sources & evidence

ORD record
ord-a4c6609011844721be67e7dce90933ad
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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