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

HRID 982297Notes

Reaction equation

HRID 982297 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].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][C:26](=O)[O:27]C2C=CC=CC=2)[N:19]=1.C1CCN2C(=NCCC2)CC1>C(#N)C.O>[CH3:16][O:17][C:18]1[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][C:26]([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:27])[N:19]=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 chloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 0.4 g of the product of Example 4 and 0.46 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-5f1cfde6efe94c1883ff7d3d5981218c
Source dataset
uspto-grants-1991_02
Patent number
US04995901

Reaction notes

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