4-Phenylsemicarbazide → HCID 59152494, compound

HRID 558169Notes

Reaction equation

HRID 558169 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([CH2:11][O:12][C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=O)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[C:22]1([NH:28][C:29](=[O:32])[NH:30][NH2:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([CH2:11][O:12][C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([NH:31][NH:30][C:29]([NH:28][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:32])=[O:17])[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 108374-PhenylsemicarbazideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 59152564HCID 59152564, compound2×

Product 1

HCID 59152494HCID 59152494, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-acetamidopyridin-4-yl)methoxybenzoic acid (500 mg, 1.8 mmol; Reference Compound 3-(1)), 4-phenylsemicarbazide (265 mg, 1.8 mmol) and diisopropylethylamine (450 μL, 2.6 mmol) in N,N-dimethylformamide (5.0 mL) was added HCTU (940 mg, 2.3 mmol) under ice-cooling, and then the mixture was stirred for 8 hours at room temperature. The reaction solution was diluted with ethyl acetate (20 mL). To the solution was added a 0.1 M aqueous sodium hydroxide solution (20 mL). The ethyl acetate layer was washed with a saturated brine solution, dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to dryness, and ethanol was added to the residue. The precipitated solid was filtered off and dried under a reduced pressure to give 250 mg (46%) of the titled compound as colorless solid.

Workup

  1. temperaturecooling
  2. washThe ethyl acetate layer was washed with a saturated brine solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure to dryness, and ethanol
  5. additionwas added to the residue
  6. filtrationThe precipitated solid was filtered off
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-e487c765dea34e8ea0cb4c6407287bc7
Source dataset
uspto-grants-2011_11
Patent number
US08063034B2

Reaction notes

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