Dimethylamine → HCID 57999028, compound

HRID 656560Notes

Reaction equation

HRID 656560 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[C:12](=[C:16](O)[CH3:17])[C:11](=O)[CH2:10]1.Cl.[NH2:21][C:22]([NH2:24])=[NH:23].CNC>CCO>[NH2:24][C:22]1[N:23]=[C:16]([CH3:17])[C:12]2[C:13](=[O:15])[CH2:14][CH:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[Br:1])[CH2:10][C:11]=2[N:21]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5742Guanidine HydrochlorideHCID 178467255HCID 178467255, compound

Product 1

HCID 57999028HCID 57999028, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
100 °C

Procedure

To a 150 mL pressure vessel was added 5-(2-bromo-4-fluorophenyl)-2-(1-hydroxyethylidene)cyclohexane-1,3-dione (1E, 1.12 g, 3.42 mmol, 1.0 eq.), EtOH (30 mL), guanidine hydrochloride (818 mg, 8.56 mmol, 2.5 eq.), and dimethylamine (2.0 M in THF, 10 mL, 20.5 mmol, 6.0 eq.). The vessel was sealed and heated for 72 hours at 100° C. LC/MS determined the reaction to be complete. The reaction was cooled and concentrated to give a pasty gray solid. EtOH (˜10 mL) was added to the residue and sonicated to give a suspension. The solid was collected by filtration and rinsed with cold EtOH to give a light-yellow solid (288 mg, 24%). ESI-MS: m/z 350.2 (M+H)+.

Workup

  1. customThe vessel was sealed
  2. customthe reaction
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. customto give a pasty gray solid
  6. customsonicated
  7. customto give a suspension
  8. filtrationThe solid was collected by filtration
  9. washrinsed with cold EtOH

Sources & evidence

ORD record
ord-f461fdb07e1d4bb8a07efd08274632ca
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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