Water → HCID 68942927, compound

HRID 1869051Notes

Reaction equation

HRID 1869051 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:12](=[O:19])[NH:13][NH:14][C:15]=2[CH:16]([CH3:18])[CH3:17])=[C:6]([CH3:20])[CH:5]=1.[CH2:21]([O:28][C:29](ON1C(=O)CCC1=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>O1CCCC1>[CH2:21]([O:28][C:29]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:12](=[O:19])[NH:13][NH:14][C:15]=2[CH:16]([CH3:17])[CH3:18])=[C:6]([CH3:20])[CH:5]=1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 83172Benzyl succinimido carbonateHCID 68942502HCID 68942502, compound

Product 1

HCID 68942927HCID 68942927, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{[4-(2-aminoethyl)-2-methylphenyl]methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (0.3 g) in tetrahydrofuran (5 mL) was added N-(benzyloxycarbonyloxy)succinimide (0.33 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution twice, water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.34 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium hydrogen carbonate solution twice
  3. dry with materialwater and brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9cea714afa3e45dfbce8e35aa95f115c
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

Loading…