Triethylamine → 4-(6-Acetoxyacetylaminomethylpyridin-2-yl)-2-[(acetoxyacetylamino)(amino)methyleneamino]thiazole

HRID 1491856Notes

Reaction equation

HRID 1491856 reaction equation
[C:1]([O:4][CH2:5][C:6](Cl)=[O:7])(=[O:3])[CH3:2].Cl.Cl.Cl.[NH2:12][CH2:13][C:14]1[N:19]=[C:18]([C:20]2[N:21]=[C:22]([N:25]=[C:26]([NH2:28])[NH2:27])[S:23][CH:24]=2)[CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.C(=O)([O-])[O-:37].[K+].[K+].[C:42]([O:45][CH2:46][CH3:47])(=[O:44])[CH3:43]>ClCCl.O.O1CCCC1>[C:1]([O:4][CH2:5][C:6]([NH:12][CH2:13][C:14]1[N:19]=[C:18]([C:20]2[N:21]=[C:22]([N:25]=[C:26]([NH:28][C:47](=[O:37])[CH2:46][O:45][C:42](=[O:44])[CH3:43])[NH2:27])[S:23][CH:24]=2)[CH:17]=[CH:16][CH:15]=1)=[O:7])(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 26297Acetoxyacetyl chlorideHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Product 1

HCID 538938594-(6-Acetoxyacetylaminomethylpyridin-2-yl)-2-[(acetoxyacetylamino)(amino)methyleneamino]thiazole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetoxyacetyl chloride (0.7 g) was added to a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.5 g) and triethylamine (2.6 ml) in dichloromethane (30 ml) under ice-cooling and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was added to a mixture of tetrahydrofuran, ethyl acetate and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was separated and purified by column chromatograpy on silica gel, and eluted with a mixture of chloroform and methanol (9:1, V/V). The eluted fast fractions containing the desired were collected and evaporated in vacuo to give 4-(6-acetoxyacetylaminomethylpyridin-2-yl)-2-[(acetoxyacetylamino)(amino)methyleneamino]thiazole (0.3 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was separated
  6. custompurified by column chromatograpy on silica gel
  7. washeluted with a mixture of chloroform and methanol (9:1, V/V)
  8. washThe eluted fast fractions
  9. additioncontaining the
  10. customdesired were collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-484ed975921a4cefaf71e1b13259d946
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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