Pyridine → HCID 22923086, compound

HRID 2257698Notes

Reaction equation

HRID 2257698 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.Cl[S:13]([C:16]1[C:25]([NH:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:15])=[O:14].[O-:32][C:33]#[N:34].[Na+].N1C=CC=CC=1>C(#N)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:33]([NH:34][S:13]([C:16]2[C:25]([NH:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])(=[O:15])=[O:14])=[O:32])[N:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 517096Sodium CyanateHCID 53969662HCID 53969662, compound

Product 1

HCID 22923086HCID 22923086, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In succession, 0.54 g of 2-amino-4,6-dimethoxypyrimidine and 1.50 g of methyl 2-chlorosulfonyl-3-(N-methoxycarbonylmethylamino)benzoate are added at room temperature to a suspension of 0.61 g of sodium cyanate, 0.8 ml of pyridine and 18 ml of acetonitrile. The reaction mixture is stirred at room temperature for 3.5 h and then poured into ice-water. For purification the sulfonylurea which is separated out is stirred in a little methanol, separated off by means of filtration and dried. The resulting N-[(4,6-dimethoxypyrimidin-2-yl)amino-carbonyl]-2-methoxycarbonyl-6-(N-methoxycarbonylmethylamino)benzenesulfonamide is obtained as a colorless solid (1.35 g) 150°-154° C.

Workup

  1. customFor purification the sulfonylurea which
  2. customis separated out
  3. stirringis stirred in a little methanol
  4. customseparated off by means of filtration
  5. customdried

Sources & evidence

ORD record
ord-647b2111991546e3a6c8d802d4698e3c
Source dataset
uspto-grants-1997_08
Patent number
US05658854

Reaction notes

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