Hydrazine hydrate (1:1) → HCID 46213965, compound

HRID 2367215Notes

Reaction equation

HRID 2367215 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([C:17]2C=C[CH:20]=[CH:19][C:18]=2OC)[N:3]=1.O.[NH2:26][NH2:27].O1[CH2:33][CH2:32][O:31][CH2:30]C1>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:11]([C:12]([NH2:13])=[N:26][NH:27]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:33][C:32]=2[O:31][CH3:30])[N:3]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 312751,4-DioxaneHCID 58504625HCID 58504625, compound

Product 1

HCID 46213965HCID 46213965, compound

Conditions

Temperature
95 °C

Procedure

To the mixture of 4-{2-Amino-6-[2-(methyloxy)phenyl]-4-pyrimidinyl}-2-fluorobenzonitrile (306 mg) in 1,4-dioxane (30 mL) was added hydrazine monohydrate (2.5 mL), and the mixture was stirred overnight at 95° C. The reaction mixture was cooled to room temperature and filtered to remove some black solid (seemed to be Pd particle). Additional hydrazine monohydrate (1 mL) was added, and the resulting mixture was stirred for another 24 hours at 95° C. The solvent was evaporated, and the resulting residue was purified by RPHPLC (CH3CN/H2O w/0.1% NH4HCO3) to afford the title compound (43 mg) as a yellow solid. LC-MS (ES) m/z=333 [M+H]+. 1HNMR (400 MHz, DMSO-d6): δ 3.88 (s, 3H), 5.42 (s, 2H), 6.66 (s, 2H), 7.08 (m, 1H), 7.18 (d, J=8.4 Hz, 1H), 7.46 (m, 1H), 7.58 (m, 2H), 7.78 (m, 2H), 7.98 (s, 1H), 11.60 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto remove some black solid (seemed to be Pd particle)
  4. additionAdditional hydrazine monohydrate (1 mL) was added
  5. stirringthe resulting mixture was stirred for another 24 hours at 95° C
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by RPHPLC (CH3CN/H2O w/0.1% NH4HCO3)

Sources & evidence

ORD record
ord-7458de05679d4a419b70e9fe840fcf9c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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