Hydrochloric Acid → HCID 66972133, compound

HRID 1469117Notes

Reaction equation

HRID 1469117 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:17]=[C:16]([F:18])[C:15]([N:19]=CN(C)C)=[N:14][C:13]2=[O:24])(=[O:11])=[O:10])=[CH:5][CH:4]=1>O1CCOCC1>[NH2:19][C:15]1[C:16]([F:18])=[CH:17][N:12]([S:9]([C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)(=[O:11])=[O:10])[C:13](=[O:24])[N:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66973322HCID 66973322, compound

Product 1

HCID 66972133HCID 66972133, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To an 8 mL screw-cap vial was added dioxane (9 mL), 1 N aqueous hydrochloric acid (HCl; 1 mL), and N′-[1-(4-chloro-benzenesulfonyl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethylformamidine (269 mg, 0.75 mmol). The mixture was shaken at room temperature for 16 h, evaporated under a stream of nitrogen, and partitioned between EtOAc and satd aq NaHCO3. The organic phase was dried over MgSO4, filtered, and evaporated to yield the title product as a white solid (196 mg, 86%): mp 174-178° C.; 1H NMR (300 MHz, CDCl3) δ 8.5 (br s, 1H), 8.08 (d, J=5.9 Hz, 1H), 8.04-7.98 (m, 2H), 7.55-7.49 (m, 2H), 5.9 (br s, 1H); ESIMS m/z 304 ([M+H]+).

Workup

  1. customTo an 8 mL screw-cap vial
  2. customevaporated under a stream of nitrogen
  3. custompartitioned between EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-bb424146db7b43c5913d4b5fe40f59ba
Source dataset
uspto-grants-2015_04
Patent number
US09006259B2

Reaction notes

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