1,8-Diazabicyclo(5.4.0)undec-7-ene → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

HRID 231976Notes

Reaction equation

HRID 231976 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([NH2:18])(=[O:17])=[O:16])=[N:5][N:4]=1.C1([O:25][C:26](=O)[NH:27][C:28]2[N:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[N:29]=2)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCOCC1.O>[CH3:35][O:34][C:32]1[CH:31]=[C:30]([O:36][CH3:37])[N:29]=[C:28]([NH:27][C:26]([NH:18][S:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][C:6]2[S:7][C:3]([S:2][CH3:1])=[N:4][N:5]=2)(=[O:16])=[O:17])=[O:25])[N:33]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 159257222-[[5-(Methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

Product 1

HCID 15925723N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamideYield 19.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension containing 0.63 g of the sulfonamide prepared in Example 3 in 10 ml of p-dioxane was added 0.6 g phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate followed by dropwise addition of 0.33 g of 1.8-diazabicyclo[5.4.0]undec-7-ene (DBU). The solution was stirred at room temperature for two hours then diluted with about 75 ml of water. After extracting the cloudy aqueous solution 1×30 ml of diethyl ether, the clear aqueous layer was acidified with concentrated hydrochloric acid (red to litmus paper), and the suspension was filtered. The residue was triturated with 5 ml of warm ethyl acetate to give 0.2 g of the subject compound; m.p. 171°-175° C. NMR (CDCl3, DMSO-d6): δ 2.7(s, SCH3); 4.0(s, OCH3); 4.95(s, CH2); 5.9(s, pyrimidine H); 7.6-8.4(m, ar); 9.8(s, NH) ppm.

Workup

  1. extractionAfter extracting the cloudy aqueous solution 1×30 ml of diethyl ether
  2. filtrationthe suspension was filtered
  3. customThe residue was triturated with 5 ml of warm ethyl acetate

Sources & evidence

ORD record
ord-218389b8d51544a09c9445abda564d0f
Source dataset
uspto-grants-1989_07
Patent number
US04851030

Reaction notes

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