Hydrochloric Acid → 5-(Cyanomethyl)-N-((4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl)-2-methoxybenzenesulfonamide

HRID 477724Notes

Reaction equation

HRID 477724 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)#[N:2].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([NH:26][C:27](=O)[O:28]C2C=CC=CC=2)[N:19]=1.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C.O>[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10]([NH:13][C:27]([NH:26][C:20]2[N:19]=[C:18]([O:17][CH3:16])[CH:23]=[C:22]([O:24][CH3:25])[N:21]=2)=[O:28])(=[O:12])=[O:11])[CH:9]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 139214555-Cyanomethyl-2-methoxybenzenesulfonamide

Product 1

HCID 139214565-(Cyanomethyl)-N-((4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl)-2-methoxybenzenesulfonamideYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 0.3 g of the compound from Example 3 and 0.37 g 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 15 ml of dry acetonitrile was added 0.198 ml DBU. After being stirred overnight the clear solution was diluted with 50 ml of water, acidified with 1N HCl and the precipitate was filtered off. The residue was washed with water and triturated with ether to give 0.44 g solid, m.p. 168°-171° C. (dec.);

Workup

  1. filtrationthe precipitate was filtered off
  2. washThe residue was washed with water
  3. customtriturated with ether

Sources & evidence

ORD record
ord-bd8a2906e35b4f798adecf1e43eec0d8
Source dataset
uspto-grants-1989_12
Patent number
US04889550

Reaction notes

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