Hydrazine hydrate (1:1) → HCID 46214647, compound

HRID 2367193Notes

Reaction equation

HRID 2367193 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]([N:17]2[CH2:20][CH2:19][CH2:18]2)[N:3]=1.O.[NH2:22][NH2:23]>CO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:11]([C:12]([NH2:13])=[N:22][NH:23]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([N:17]2[CH2:20][CH2:19][CH2:18]2)[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58504573HCID 58504573, compound

Product 1

HCID 46214647HCID 46214647, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

In a 25 mL sealable tube were combined 4-[2-amino-6-(1-azetidinyl)-4-pyrimidinyl]-2-fluorobenzonitrile (0.21 g, 0.79 mmol), hydrazine monohydrate (0.77 mL, 15.8 mmol) and CH3OH (10 mL). The vial was sealed, and the reaction mixture was stirred overnight at 95° C. The reaction was concentrated, and the resulting yellow solid was diluted with EtOH (2 mL) and water (5 mL). The mixture was sonicated, and the solid was filtered, washed with water, and dried under vacuum to afford the title compound (99 mg, 43%) as a light yellow solid. LC-MS (ES) m/z=282 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 2.33 (m, 2H), 4.02 (m, 4H), 5.38 (s, 2H), 6.13 (bs, 2H), 6.14 (s, 1H), 7.51 (dd, J=8.3, 1.3 Hz, 1H), 7.70 (d, J=8.3 Hz, 1H), 7.91 (s, 1H), 11.50 (s, 1H).

Workup

  1. customIn a 25 mL sealable tube were combined
  2. customThe vial was sealed
  3. concentrationThe reaction was concentrated
  4. additionthe resulting yellow solid was diluted with EtOH (2 mL) and water (5 mL)
  5. customThe mixture was sonicated
  6. filtrationthe solid was filtered
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-9f3a9475821e49d49012b648aab90ee4
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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