Hydrazine hydrate (1:1) → HCID 46214810, compound

HRID 2367195Notes

Reaction equation

HRID 2367195 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[N:12]=[C:11]([N:21](C)[C:22](=O)C)[N:10]=2)=[CH:5][C:4]=1F)#[N:2].O.[NH2:28][NH2:29]>CCO>[CH3:22][NH:21][C:11]1[N:10]=[C:9]([C:6]2[CH:5]=[C:4]3[C:3]([C:1]([NH2:2])=[N:28][NH:29]3)=[CH:8][CH:7]=2)[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58504629HCID 58504629, compound

Product 1

HCID 46214810HCID 46214810, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

In a 25 mL sealable tube were combined N-[4-(4-cyano-3-fluorophenyl)-6-(1-piperidinyl)-2-pyrimidinyl]-N-methylacetamide (0.04 g, 0.11 mmol) and hydrazine monohydrate (0.11 mL, 2.21 mmol) in EtOH (10 mL). The tube was sealed, and the reaction mixture was stirred overnight at 95° C. The reaction was cooled to room temperature and concentrated. The resulting oil was dissolved in EtOH (3 mL) followed by the addition of water (6 mL). Since no solid was observed (a yellow oil was formed), the mixture was concentrated to dryness. The resulting oil was diluted with CH3CN (2 mL) and sonicated. The resulting yellow solid was filtered, washed with CH3CN (1 mL) and dried to afford the title compound (18 mg, 48%). LC-MS (ES) m/z=324 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.60 (m, 4H), 1.68 (m, 2H), 2.92 (d, J=4.3 Hz, 3H), 3.84 (bs, 4H), 5.54 (bs, 2H), 6.81 (bs, 1H), 7.21 (bs, 1H), 7.40 (bs, 1H), 7.76 (bs, 1H), 7.85 (d, J=8.3 Hz, 1H), 11.83 (bs, 1H).

Workup

  1. customIn a 25 mL sealable tube were combined
  2. customThe tube was sealed
  3. temperatureThe reaction was cooled to room temperature
  4. concentrationconcentrated
  5. dissolutionThe resulting oil was dissolved in EtOH (3 mL)
  6. additionfollowed by the addition of water (6 mL)
  7. customwas formed), the mixture
  8. concentrationwas concentrated to dryness
  9. additionThe resulting oil was diluted with CH3CN (2 mL)
  10. customsonicated
  11. filtrationThe resulting yellow solid was filtered
  12. washwashed with CH3CN (1 mL)
  13. customdried

Sources & evidence

ORD record
ord-e7ed319dcb1744239a21ea091bd9b545
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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