Ethanol → HCID 46215124, compound

HRID 2367575Notes

Reaction equation

HRID 2367575 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[CH3:21])[N:13]=[C:12]([NH:22][CH3:23])[N:11]=2)[CH:7]=[C:6]([O:24][CH3:25])[C:3]=1[C:4]#[N:5].CCO.CCN(C(C)C)C(C)C.[NH2:38][NH2:39]>O>[CH3:23][NH:22][C:12]1[N:11]=[C:10]([C:8]2[CH:9]=[C:2]3[C:3]([C:4]([NH2:5])=[N:38][NH:39]3)=[C:6]([O:24][CH3:25])[CH:7]=2)[CH:15]=[C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[CH3:21])[N:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 58504665HCID 58504665, compound

Product 1

HCID 46215124HCID 46215124, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Into a sealable tube, 2-fluoro-4-{2-(methylamino)-6-[(2R)-2-methyl-1-pyrrolidinyl]-4-pyrimidinyl}-6-(methyloxy)benzonitrile (100 mg, 0.293 mmol), EtOH (5 mL), Hunig's base (0.05 mL, 0.29 mmol), and hydrazine anhydrous (0.055 mL, 1.76 mmol) were added, and the yellow suspension mixture was heated overnight at 110° C. in an oil bath. After overnight, there was yellow suspension as well as some black colored solid formed. LCMS showed mainly product. The reaction was cooled to room temperature. Water (20 mL) was added to the yellow solution, and a solid was formed. The solid was filtered, washed by water, and dried in vacuum. The solid was purified further by flash column chromatography. The fractions with product were combined, and the solvent was removed under reduced pressure to afford the title compound (23.7 mg) as a white solid. LC-MS (ES) m/z=354 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 1.30 (d, J=6.3 Hz, 3H), 1.75-2.18 (m, 4H), 3.02 (s, 3H), 3.50-3.63 (m, 2H), 4.02 (s, 3H), 4.34 (m, 1H), 4.50 (m, 2H), 6.07 (s, 1H), 6.93 (s, 1H), 7.44 (s, 1H).

Workup

  1. customformed
  2. temperatureThe reaction was cooled to room temperature
  3. customa solid was formed
  4. filtrationThe solid was filtered
  5. washwashed by water
  6. customdried in vacuum
  7. customThe solid was purified further by flash column chromatography
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c043185e0c1f4c828f60027648a5229d
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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