1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 53768911, compound

HRID 2399589Notes

Reaction equation

HRID 2399589 reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12]([O:14][C:15]([NH:17][C:18]([CH2:20][NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:32]([O:34][CH3:35])=[O:33])=[C:26]([S:28]([NH2:31])(=[O:30])=[O:29])[CH:27]=1)=[S:19])=[O:16])[CH3:13].[CH3:36][O:37][C:38]1[CH:43]=[C:42]([O:44][CH3:45])[N:41]=[C:40]([NH:46][C:47](OC2C=CC=CC=2)=[O:48])[N:39]=1>C(#N)C>[CH3:45][O:44][C:42]1[CH:43]=[C:38]([O:37][CH3:36])[N:39]=[C:40]([NH:46][C:47]([NH:31][S:28]([C:26]2[CH:27]=[C:22]([NH:21][CH2:20][C:18]([NH:17][C:15]([O:14][CH2:12][CH3:13])=[O:16])=[S:19])[CH:23]=[CH:24][C:25]=2[C:32]([O:34][CH3:35])=[O:33])(=[O:29])=[O:30])=[O:48])[N:41]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 54425868HCID 54425868, compound

Product 1

HCID 53768911HCID 53768911, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.2 ml of DBU is added to a suspension of 0.69 g (1.84 mmol) of 5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide and 0.55 g (1.99 mmol) of 4,6-dimethoxy-2-phenoxycarbonylaminopyrimidine in 5 ml of acetonitrile. The mixture is stirred for 17 h at room temperature and the solvent is then removed by distillation. The residue is taken up in water and washed with diethyl ether. The aqueous phase is acidified with concentrated hydrochloric acid (pH=1) and produces a colorless precipitate, which is filtered off and induced to crystallize by stirring with a little methanol. The resulting product is 0.61 g (60% of theory) of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide. m.p.: 144°-145° C.

Workup

  1. customthe solvent is then removed by distillation
  2. washwashed with diethyl ether
  3. customproduces a colorless precipitate, which
  4. filtrationis filtered off
  5. customto crystallize
  6. stirringby stirring with a little methanol

Sources & evidence

ORD record
ord-28c736ce65a1455aaa4367c078f213c4
Source dataset
uspto-grants-1995_09
Patent number
US05449812

Reaction notes

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