Hydrochloric Acid → Methyl 4-cyclopentylidenehydrazino-2-[3-(4,6-dimethoxypyrimidin-2-yl)-ureidosulfonyl]benzoate

HRID 1385865Notes

Reaction equation

HRID 1385865 reaction equation
[C:1]1(=[N:6][NH:7][C:8]2[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]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[N:27]=[C:26]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)[N:25]=1.N12CCCN=C1CCCCC2.Cl>O.C(#N)C>[C:1]1(=[N:6][NH:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([S:18]([NH:19][C:33]([NH:32][C:26]3[N:25]=[C:24]([O:23][CH3:22])[CH:29]=[C:28]([O:30][CH3:31])[N:27]=3)=[O:34])(=[O:20])=[O:21])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]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 15300841Methyl 4-cyclopentylidenehydrazino-2-sulfamoylbenzoate

Product 1

HCID 15300842Methyl 4-cyclopentylidenehydrazino-2-[3-(4,6-dimethoxypyrimidin-2-yl)-ureidosulfonyl]benzoateYield 65.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1.5 g (4.8 mmol) of methyl 4-cyclopentylidenehydrazino-2-sulfamoylbenzoate and 1.6 g (5.8 mmol) of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate are initially introduced into 20 ml of acetonitrile. 1.6 g (10.6 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are 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 hydrochloric acid. The aqueous phase is extracted three times with CH2Cl2. After the methylene chloride phase has been washed with 2N hydrochloric acid and water, it is dried and evaporated. The residue is triturated with diisopropyl ether. After filtering off with suction and drying, 1.55 g (65% of theory) of methyl 4-cyclopentylidenehydrazino-2-[3-(4,6-dimethoxypyrimidin-2-yl)-ureidosulfonyl]benzoate of melting point 168-170° C. (decomposition) are obtained.

Workup

  1. extractionThe aqueous phase is extracted three times with CH2Cl2
  2. washAfter the methylene chloride phase has been washed with 2N hydrochloric acid and water, it
  3. customis dried
  4. customevaporated
  5. customThe residue is triturated with diisopropyl ether
  6. filtrationAfter filtering off with suction
  7. customdrying

Sources & evidence

ORD record
ord-35c4f2b0c77a4c3b92f9b30f902f0a3d
Source dataset
uspto-grants-2001_07
Patent number
US06265348B1

Reaction notes

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