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

HRID 581659Notes

Reaction equation

HRID 581659 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 2 N hydrochloric acid. The aqueous phase is extracted three times with CH2Cl2. After the methylene chloride phase has been washed with 2 N 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 2 N 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-27c06531b71244e0be071a9212bdb58c
Source dataset
uspto-grants-1999_07
Patent number
US05922645

Reaction notes

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