Hydrochloric Acid → HCID 9970997, compound

HRID 1684103Notes

Reaction equation

HRID 1684103 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]([N+:22]([O-])=O)=[C:7]([O:20][CH3:21])[C:8]([C:16](=[O:19])[NH:17][CH3:18])=[C:9]([N+:13]([O-])=O)[C:10]=1[O:11][CH3:12])=[O:4].CO.Cl>[Pd].C(O)CCC.C(O)(=O)C.O>[CH3:18][NH:17][C:16]([C:8]1[C:9]([NH2:13])=[C:10]([O:11][CH3:12])[C:5]([C:3](=[O:4])[NH:2][CH3:1])=[C:6]([NH2:22])[C:7]=1[O:20][CH3:21])=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10360001HCID 10360001, compound

Product 1

HCID 9970997HCID 9970997, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22056973Butanol acetic acid waterSolvent

Procedure

A mixture consisting of 978 mg (2.84 mmol) of 7, 100 mg 5% Pd/C, and 100 mL of methanol was shaken under 50 psi of H2 for 4 hours. Upon completing the reduction, 10 mL of concentrated hydrochloric acid was added to the reaction mixture with stirring. After filtering the solution through CELITE and washing the filtrate with methanol, the solvent was removed in vacuo and the residue dried for several hours. The dihydrochloride salt of 9 was recrystallized by dissolution in a minimum amount of hot methanol followed by cooling and then addition of ethyl acetate: 893 mg (88%) yield; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.44; 1H NMR (dimethyl-d6 sulfoxide) δ8.40 (2H, brs, 3- and 6-carbamyl proton), 3.64 (6H, s, methoxys), 2.81 (6H, d, J=4.0 Hz, 3- and 6-carbamyl methyls); mass spectrum (EI mode), m/z 282 (P+).

Workup

  1. additionwas added to the reaction mixture
  2. stirringwith stirring
  3. filtrationAfter filtering the solution through CELITE
  4. washwashing the filtrate with methanol
  5. customthe solvent was removed in vacuo
  6. customthe residue dried for several hours
  7. customThe dihydrochloride salt of 9 was recrystallized by dissolution in a minimum amount of hot methanol
  8. temperatureby cooling
  9. additionaddition of ethyl acetate
  10. custom893 mg (88%) yield

Sources & evidence

ORD record
ord-13b0e745190743d1b0aca3c8d01b21bc
Source dataset
uspto-grants-1997_06
Patent number
US05639881

Reaction notes

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