Hydrochloric Acid → HCID 18354197, compound

HRID 429033Notes

Reaction equation

HRID 429033 reaction equation
N12CCCN=C1CCCCC2.[CH:12]([NH:14][C:15]1[C:16]([S:21]([NH2:24])(=[O:23])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:13].[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[N:30]=[C:29]([N:35](C2C=CC=CC=2)[C:36](=O)[O-:37])[N:28]=1.Cl>C(#N)C.O>[CH3:34][O:33][C:31]1[CH:32]=[C:27]([O:26][CH3:25])[N:28]=[C:29]([NH:35][C:36]([NH:24][S:21]([C:16]2[C:15]([NH:14][CH:12]=[O:13])=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:23])=[O:22])=[O:37])[N:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18354198HCID 18354198, compoundHCID 22104197HCID 22104197, compound

Product 1

HCID 18354197HCID 18354197, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

0.75 g (0.0049 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is added to a solution of 0.5 g (0.0019 mol) of 3-formylamino-2-pyridinesulfonamide and 0.68 g (0.0025 mol) of N-(4,6-dimethoxypyrimidin-2-yl)phenylcarbamate in 40 ml of acetonitrile. The solution is stirred for 16 hours at room temperature, 20 ml of water are subsequently added, and the pH is brought to 4 using 2-normal hydrochloric acid. The mixture is extracted with dichloromethane, the organic phase is dried over MgSO4, and n-heptane is added. Filtration gives 0.64 g (89% of theory) of N-[(4,6-dimethoxy-pyrimidin-2-yl)-aminocarbonyl]-3-formylamino-2-pyridinesulfonamide of melting point 172° C. (decomp.).

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. dry with materialthe organic phase is dried over MgSO4, and n-heptane
  3. additionis added
  4. filtrationFiltration

Sources & evidence

ORD record
ord-b4eaf252c1204b8cadb85345c49c0dc2
Source dataset
uspto-grants-2001_11
Patent number
US06316388B1

Reaction notes

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