1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-[[(4-Methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]aminosulfonyl]-N-methoxybenzenecarboximidoyl chloride

HRID 1164726Notes

Reaction equation

HRID 1164726 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([Cl:15])=[N:12][O:13][CH3:14])(=[O:4])=[O:3].C1([O:22][C:23](=O)[NH:24][C:25]2[N:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([CH3:33])[N:26]=2)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C(#N)C.O>[CH3:32][O:31][C:29]1[CH:28]=[C:27]([CH3:33])[N:26]=[C:25]([NH:24][C:23]([NH:1][S:2]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:11]([Cl:15])=[N:12][O:13][CH3:14])(=[O:3])=[O:4])=[O:22])[N:30]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13577349Phenyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 540187652-(Aminosulfonyl)-N-methoxybenzenecarboximidoyl chloride

Product 1

HCID 537866242-[[(4-Methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]aminosulfonyl]-N-methoxybenzenecarboximidoyl chlorideYield 52.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 0.4 g of the product of Example 4 and 0.46 g of phenyl(4-methoxy-6-methylpyrimidin-2-yl)carbamate in 10 ml of dry acetonitrile was added 0.25 g of DBU. The suspension was stirred for about two hours at room temperature, then diluted with excess water and filtered. The filtrate was acidified with concentrated hydrochloric acid to yield a precipitate. After filtration, the residue was washed with excess water and suction-dried to yield 0.35 g of the subject compound, m.p. 178° to 179° C.;

Workup

  1. filtrationfiltered
  2. customto yield a precipitate
  3. filtrationAfter filtration
  4. washthe residue was washed with excess water
  5. customsuction-dried

Sources & evidence

ORD record
ord-7922528f22594bbe8e11c38d22122967
Source dataset
uspto-grants-1990_03
Patent number
US04906282

Reaction notes

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