Lithium Hydroxide → HCID 25051759, compound

HRID 1818022Notes

Reaction equation

HRID 1818022 reaction equation
C([O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH2:13][CH:14]2[NH:19][C:20]([NH:22][CH2:23][CH2:24][F:25])=[O:21])(=O)C1C=CC=CC=1.[OH-].[Li+]>CO>[F:25][CH2:24][CH2:23][NH:22][C:20]([NH:19][CH:14]1[C:15]2[C:11](=[C:10]([OH:9])[CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:21]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 25051758HCID 25051758, compound

Product 1

HCID 25051759HCID 25051759, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-({[(2-fluoroethyl)amino]carbonyl} amino)-2,3-dihydro-1H-inden-4-yl benzoate (reported earlier, 230 mg, 0.67 mmol) was dissolved in MeOH (20 mL) and lithium hydroxide (900.00 mg, 37.58 mmol) was added. The resulting reaction mixture was refluxed for 4 hours and then cooled to room temperature. Concentration followed by the addition of HCl (10%, 10.00 mL) gave a precipitate. The solid was then washed with water, ether and then vacuum-dried to afford the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.53-1.68 (m, 1H) 2.27-2.41 (m, 1H) 2.47-2.61 (m, 1H) 2.70-2.85 (m, 1H) 3.24-3.39 (m, 2H) 4.31 (t, J=5.13 Hz, 1H) 4.47 (t, J=4.98 Hz, 1H) 4.97-5.10 (m, 1H) 6.03 (t, J=5.57 Hz, 1H) 6.25 (d, J=8.21 Hz, 1H) 6.58-6.72 (m, 2H) 6.97 (t, J=7.77 Hz, 1H) 9.24 (s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 4 hours
  3. concentrationConcentration
  4. additionfollowed by the addition of HCl (10%, 10.00 mL)
  5. customgave a precipitate
  6. washThe solid was then washed with water, ether
  7. customvacuum-dried

Sources & evidence

ORD record
ord-386f340d9abb484e9ce9fa422d580ce9
Source dataset
uspto-grants-2009_10
Patent number
US07598417B2

Reaction notes

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