Hydrochloric Acid → 3,4-Dihydro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]-1-oxo-1H-pyrrolo[2,1-c][1,4]-oxazine-8-sulfonamide

HRID 1707930Notes

Reaction equation

HRID 1707930 reaction equation
[O:1]=[C:2]1[C:7]2=[C:8]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:9]=[CH:10][N:6]2[CH2:5][CH2:4][O:3]1.[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH:24][C:25](=O)[O:26]C2C=CC=CC=2)[N:18]=1.N12CCCN=C1CCCCC2.Cl>C(#N)C.C(OCC)C.O>[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH:24][C:25]([NH:14][S:11]([C:8]2[CH:9]=[CH:10][N:6]3[CH2:5][CH2:4][O:3][C:2](=[O:1])[C:7]=23)(=[O:13])=[O:12])=[O:26])[N:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11448329Carbamic acid, (4-methoxy-6-methyl-1,3,5-triazin-2-yl)-, phenyl esterHCID 189604133,4-dihydro-1-oxo-1H-pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide

Product 1

HCID 189604023,4-Dihydro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]-1-oxo-1H-pyrrolo[2,1-c][1,4]-oxazine-8-sulfonamideYield 56.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 40 mg (0.185 mmol) of 3,4-dihydro-1-oxo-1H-pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide and 53 mg (0.204 mmol) of phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate in 0.8 mL acetonitrile was treated with 0.03 mL 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and then stirred 40 minutes at ambient temperature. Water (5 mL) plus 0.5 mL 1N HCl was added with stirring followed by ca. 1 mL of ethyl ether. The product crystallized from the two phase mixture and was collected by filtration to afford 40 mg of the title compound, m.p. 204°-207° C. dec.

Workup

  1. stirringwith stirring
  2. customThe product crystallized from the two phase mixture
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-3b7f1bfa32c94f0893791965d8a29a1b
Source dataset
uspto-grants-1994_10
Patent number
US05356862

Reaction notes

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