Acetic Acid → HCID 14350432, compound

HRID 1381469Notes

Reaction equation

HRID 1381469 reaction equation
N12CCCN=C1CCCCC2.[CH3:12][N:13]([CH3:27])[S:14]([C:17]1[C:18]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15].[Cl:28][C:29]1[N:34]=[C:33]([NH:35][C:36](=O)[O:37]C2C=CC=CC=2)[C:32](=[O:45])[N:31]([CH3:46])[CH:30]=1.C(O)(=O)C>C(#N)C>[Cl:28][C:29]1[N:34]=[C:33]([NH:35][C:36]([NH:26][S:23]([C:18]2[C:17]([S:14]([N:13]([CH3:27])[CH3:12])(=[O:16])=[O:15])=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:25])=[O:24])=[O:37])[C:32](=[O:45])[N:31]([CH3:46])[CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13371850N1,N1-dimethylbenzene-1,2-disulfonamideHCID 14350431phenyl N-(5-chloro-1-methylpyrazin-2-on-3-yl)-carbamate

Product 1

HCID 14350432HCID 14350432, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.30 mL, 2.00 mmol) was added dropwise over two minutes to a mixture of N,N-dimethyl-1,2-benzenedisulfonamide (0.53 g, 2.00 mmol) and phenyl (6-chloro-3,4-dihydro-4-methyl-3-oxopyrazin-2-yl)carbamate (0.56 g, 2.00 mmol) in anhydrous acetonitrile (20 mL) under nitrogen. After 3 hours at room temperature, glacial acetic acid (0.12 mL, 2.10 mmol) was added. The solvent was rotary evaporated and the residue was chromatographed on a column of silica gel using a solvent mixture of 1:1 dichloromethane-ether containing 2 mL/L acetic acid as eluant. The appropriate fractions were evaporated to leave 0.76 g of N'-[(6-chloro-3,4-dihydro-4-methyl-3-oxopyrazin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide as a crystalline solid melting at 227°-230° C.

Workup

  1. customThe solvent was rotary evaporated
  2. customthe residue was chromatographed on a column of silica gel using
  3. additiona solvent mixture of 1:1 dichloromethane-ether containing 2 mL/L acetic acid as eluant
  4. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-5aca0063bcd74be3b8f0b3aaca823795
Source dataset
uspto-grants-1989_02
Patent number
US04802908

Reaction notes

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