Hydrochloric Acid → HCID 15029430, compound

HRID 1588454Notes

Reaction equation

HRID 1588454 reaction equation
[N:1]1([S:6]([CH:9]([S:11]([NH2:14])(=[O:13])=[O:12])[CH3:10])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19]([NH:25][C:26](=O)[O:27]C2C=CC=CC=2)[N:18]=1.N12CCCN=C1CCCCC2.Cl>C(#N)C>[CH3:24][O:23][C:21]1[CH:22]=[C:17]([O:16][CH3:15])[N:18]=[C:19]([NH:25][C:26](=[O:27])[NH:14][S:11]([CH:9]([S:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:7])=[O:8])[CH3:10])(=[O:13])=[O:12])[N:20]=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 15029429HCID 15029429, compound

Product 1

HCID 15029430HCID 15029430, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3.6 g (0.015 mol) of 1-pyrrolidinosulfonylethanesulfonamide (Example 1a) and 4.0 g (0.019 mol) of phenyl 4,6-dimethoxypyrimidin-2-ylcarbamate in 40 ml of acetonitrile there are added 2.9 g (0.019 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After the mixture has been stirred for five hours at room temperature, it is treated with 250 ml of ice/water and acidified with HCl to pH 2. Extraction with dichloromethane, drying and evaporation give crude 3-(4,6-dimethoxypyrimidin-2-yl)-1-(1-pyrrolidinosulfonylethylsulfonyl)urea, which is purified by trituration with diisopropyl ether (yield: 4.6 g; 73% of theory; melting point 145°-146° C.).

Workup

  1. extractionExtraction with dichloromethane
  2. customdrying
  3. customevaporation

Sources & evidence

ORD record
ord-733e836dec4e4f43a75f4f22ce23a780
Source dataset
uspto-grants-1993_06
Patent number
US05223017

Reaction notes

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