Hydrochloric Acid → HCID 15300823, compound

HRID 1457523Notes

Reaction equation

HRID 1457523 reaction equation
[C:1]([NH:6][NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([S:18](=[O:21])(=[O:20])[NH2:19])[CH:9]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].C1([O:28][C:29](=O)[NH:30][C:31]2[N:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([O:39][CH3:40])[N:32]=2)C=CC=CC=1.N12CCCN=C1CCCCC2.Cl>O.C(#N)C>[CH3:38][O:37][C:35]1[CH:34]=[C:33]([O:39][CH3:40])[N:32]=[C:31]([NH:30][C:29](=[O:28])[NH:19][S:18]([C:10]2[CH:9]=[C:8]([NH:7][NH:6][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH:17]=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])(=[O:20])=[O:21])[N:36]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 15300822HCID 15300822, compound

Product 1

HCID 15300823HCID 15300823, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

0.8 g (2.5 mmol) of methyl 4-(2-isobutyrylhydrazino)-2-sulfamoylbenzoate and 0.77 g (2.8 mmol) of phenyl-N-(4,6-dimethoxypyrimidin-2-yl)carbamate are initially introduced into 25 ml of acetonitrile. 0.83 g (5.6 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is added dropwise at 0° C. and the mixture is stirred at this temperature for 2 hours. It is poured into water and the pH is brought to 2-3 with 2N HCl. The aqueous phase is extracted three times with CH2Cl2. After the CH2Cl2 phase has been washed with 2N HCl and water, it is dried and evaporated. The residue is triturated with diethyl ether. Filtration with suction and drying gives 0.8 g (64% of theory) of methyl 2-[3-(4,6-dimethoxypyrimidin-2-yl)-ureidosulfonyl]-4-(2-isobutyrylhydrazino)benzoate of melting point 169°-171° C. (decomposition).

Workup

  1. extractionThe aqueous phase is extracted three times with CH2Cl2
  2. washAfter the CH2Cl2 phase has been washed with 2N HCl and water, it
  3. customis dried
  4. customevaporated
  5. customThe residue is triturated with diethyl ether
  6. filtrationFiltration with suction
  7. customdrying

Sources & evidence

ORD record
ord-8a5c3e3733854c7689fe0e130310591d
Source dataset
uspto-grants-1998_12
Patent number
US05849666

Reaction notes

Loading…