Hydrazine → HCID 58504795, compound

HRID 2367472Notes

Reaction equation

HRID 2367472 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22]C=[CH:20][CH:19]=3)=[O:15])[CH2:9]2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26](F)[CH:25]=2)[N:3]=1.CC[N:35](C(C)C)C(C)C.[NH2:42][NH2:43]>CCO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([NH:16][CH2:17][C:18]3[CH:19]=[CH:20][N:35]=[CH:22][CH:23]=3)=[O:15])[CH2:9]2)[CH:5]=[C:4]([C:24]2[CH:25]=[C:26]3[C:27]([C:30]([NH2:31])=[N:42][NH:43]3)=[CH:28][CH:29]=2)[N:3]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 58504591HCID 58504591, compound

Product 1

HCID 58504795HCID 58504795, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(phenylmethyl)-3-piperidinecarboxamide (190 mg, 0.440 mmol), 3 mL of EtOH, Hunig's base (0.31 mL, 1.76 mmol), and hydrazine anhydrous (0.083 mL, 2.64 mmol) were added, and the yellow mixture was heated at 150° C. for 180 minutes under microwave conditions. The solution turned black. LCMS showed mainly product. The black solids were filtered and the yellow filtrate was evaporated. The yellow residue was sonicated in EtOAc at 50° C., and the solid was filtered. This material was then sonicated in water at 50° C., and the solid was filtered and washed with water to afford the title compound (92 mg) as a light yellow solid. LC-MS (ES) m/z=444 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.37-1.55 (m, 1H), 1.62-1.80 (m, 2H), 1.96 (m, 1H), 2.35-2.45 (m, 1H), 2.81-3.05 (m, 2H), 4.18-4.46 (m, 3H), 4.56 (m, 1H), 5.38 (s, 2H), 6.10 (s, 2H), 6.65 (s, 1H), 7.25 (d, J=5.8 Hz, 2H), 7.59 (dd, J=8.6, 1.3 Hz, 1H), 7.67-7.78 (m, 1H), 7.96 (s, 1H), 8.45-8.65 (m, 3H), 11.51 (s, 1H).

Workup

  1. filtrationThe black solids were filtered
  2. customthe yellow filtrate was evaporated
  3. customThe yellow residue was sonicated in EtOAc at 50° C.
  4. filtrationthe solid was filtered
  5. customThis material was then sonicated in water at 50° C.
  6. filtrationthe solid was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-31764da53c224d13be32a62c8cef50b2
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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