Hydrochloric Acid → Methyl [[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate

HRID 34513Notes

Reaction equation

HRID 34513 reaction equation
[NH2:1][S:2]([C:5]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:6]=1)(=[O:4])=[O:3].C1([O:26][C:27](=O)[NH:28][C:29]2[N:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[N:30]=2)C=CC=CC=1.N12CCCN=C1CCCCC2.Cl>C(#N)C>[CH3:36][O:35][C:33]1[CH:32]=[C:31]([O:37][CH3:38])[N:30]=[C:29]([NH:28][C:27]([NH:1][S:2]([C:5]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][N:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:6]=2)(=[O:3])=[O:4])=[O:26])[N:34]=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 19869222Methyl 3-(aminosulfonyl)-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 86741857Methyl [[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

280 mg of Methyl 3-(aminosulfonyl)-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate and phenyl(4,6-dimethoxy-2-pyrimidinyl)carbamate were dissolved in 10 mL of acetonitrile. 1,8-Diazabicyclo[5.4.0]undec-7-ene, 0.15 mL, was added, and the reaction was stirred one hour. The solution was diluted with 30 mL of ice-water and made acidic with concentrated hydrochloric acid. The solid that separated was collected to afford 260 mg of the title compound melting 183°-188° C.

Workup

  1. customThe solid that separated
  2. customwas collected

Sources & evidence

ORD record
ord-d1f4bd8735664836bdfa20a6566a1ce7
Source dataset
uspto-grants-1988_08
Patent number
US04762550

Reaction notes

Loading…