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

HRID 2232025Notes

Reaction equation

HRID 2232025 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-253e6417f6e043f3a6b497e2ec8566d1
Source dataset
uspto-grants-1988_11
Patent number
US04786314

Reaction notes

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