Ethanol → HCID 58504528, compound

HRID 2367578Notes

Reaction equation

HRID 2367578 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([C:12]2[CH:17]=[C:16]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH3:23])[N:15]=[C:14]([NH:24][CH3:25])[N:13]=2)[CH:9]=[C:8](F)[C:5]=1[C:6]#[N:7])[CH3:2].CCO.CCN(C(C)C)C(C)C.[NH2:39][NH2:40]>O>[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([C:12]2[CH:17]=[C:16]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH3:23])[N:15]=[C:14]([NH:24][CH3:25])[N:13]=2)[CH:9]=[C:8]2[C:5]=1[C:6]([NH2:7])=[N:39][NH:40]2)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 58504838HCID 58504838, compound

Product 1

HCID 58504528HCID 58504528, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

In a sealable tube, 2-(ethyloxy)-6-fluoro-4-{2-(methylamino)-6-[(2R)-2-methyl-1-pyrrolidinyl]-4-pyrimidinyl}benzonitrile (87 mg, 0.245 mmol), EtOH (5 mL), Hunig's base (0.046 mL, 1.469 mmol), and hydrazine anhydrous (0.043 mL, 0.245 mmol) were added, and the yellow suspension mixture was heated at 100° C. overnight in an oil bath. After overnight, there was a yellow solution as well as a little amount of white colored solid formed. LCMS showed no more starting material. 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 by flash column chromatography. The fractions containing product were combined, and the solvent was removed under reduced pressure to afford the title compound (48 mg) as a white solid. LC-MS (ES) m/z=368 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.21 (d, J=6.1 Hz, 3H), 1.44 (t, J=7.0 Hz, 3H), 1.66 (m, 1H), 2.02 (m, 3H), 2.82 (d, J=4.8 Hz, 3H), 3.56 (m, 1H), 4.12-4.24 (q, J=7.1 Hz, 2H), 4.99 (s, 2H), 6.19 (s, 1H), 6.32-6.51 (m, 1H), 6.87-6.98 (m, H), 7.41-7.56 (m, 1H), 11.50 (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 by flash column chromatography
  8. additionThe fractions containing product
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b81b0937c55146b8bb9216432ba6ee89
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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