Hydrochloric Acid → HCID 11070895, compound

HRID 1976528Notes

Reaction equation

HRID 1976528 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([S:17](=[O:20])(=[O:19])[NH2:18])[CH:8]=1)=[O:6])([CH3:3])[CH3:2].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)[N:24]=1.N12CCCN=C1CCCCC2.Cl>C(#N)C>[CH3:30][O:29][C:27]1[CH:28]=[C:23]([O:22][CH3:21])[N:24]=[C:25]([NH:31][C:32](=[O:33])[NH:18][S:17]([C:9]2[CH:8]=[C:7]([C:5](=[O:6])[NH:4][CH:1]([CH3:3])[CH3:2])[CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])(=[O:20])=[O:19])[N:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 11141109HCID 11141109, compound

Product 1

HCID 11070895HCID 11070895, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.6 g (8.6 mmol) of methyl 4-isopropylcarbamoyl-2-sulfamoylbenzoate and 2.8 g (10.3 mmol) of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate were initially charged in 50 ml of acetonitrile. At room temperature, 2.9 g (19 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added dropwise, and the mixture was stirred at this temperature for 3 h. The mixture was poured into ice-water and the pH was adjusted to 1 using 2N hydrochloric acid. The precipitated solid was filtered off with suction and washed with water. After drying, 3.9 g (94% of theory) of methyl 2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-isopropylcarbamoylbenzoate of m.p. 149-151° C. (decomp.) were obtained.

Workup

  1. filtrationThe precipitated solid was filtered off with suction
  2. washwashed with water
  3. customAfter drying

Sources & evidence

ORD record
ord-65f58712215746dd96f323f83f4df4d2
Source dataset
uspto-grants-2001_05
Patent number
US06228808B1

Reaction notes

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