Semicarbazide hydrochloride → HCID 76808984, compound

HRID 449303Notes

Reaction equation

HRID 449303 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=O)[CH3:22])=[CH:19][CH:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[Na+].Cl.[NH2:30][NH:31][C:32]([NH2:34])=[O:33]>C(O)C>[N:1]1[C:10]2[C:9](=[CH:8][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=[N:30][NH:31][C:32]([NH2:34])=[O:33])[CH3:22])=[CH:19][CH:20]=[C:15]4[N:14]=[N:13]3)=[CH:6][CH:5]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 58514909HCID 58514909, compound

Product 1

HCID 76808984HCID 76808984, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of example 208 (0.070 g, 0.230 mmol) in ethanol (2 ml), sodium acetate (0.018 g, 0.230 mmol) and semicarbazide hydrochloride (0.026 g, 0.230 mmol) were added and stirred at RT for 12 h. The reaction mixture was concentrated and the residue was washed with bicarbonate solution, dichloromethane and dried under vacuum to afford the title compound as a yellow solid (0.040 g, 48%). M.P.: 249-250° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 9.70 (s, 1H), 8.88 (d, J=2.8 Hz, 1H), 8.54 (d, J=8.9 Hz, 1H), 8.45 (d, J=8.9 Hz, 1H), 8.37 (d, J=8.2 Hz, 1H), 8.01 (s, 1H), 7.99 (d, J=8.6 Hz, 1H), 7.81 (dd, J=8.6, 1.3 Hz, 1H), 7.53 (dd, J=8.2, 4.1 Hz, 1H), 6.78 (br s, 2H), 6.14 (s, 2H), 2.35 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with bicarbonate solution, dichloromethane
  3. customdried under vacuum

Sources & evidence

ORD record
ord-3c5bc668131e45e2bd946080b65ecb18
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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