Water → HCID 67842295, compound

HRID 1491869Notes

Reaction equation

HRID 1491869 reaction equation
Cl.Cl.Cl.NC[C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1.[CH2:21](N(CC)CC)C.[CH3:28][O:29][CH2:30]C(Cl)=O.O.C[N:36](C)[CH:37]=[O:38]>>[NH2:20][C:18](=[N:17][C:14]1[S:15][CH:16]=[C:12]([C:10]2[C:9]([CH3:21])=[CH:8][CH:7]=[C:6]([NH:36][C:37](=[O:38])[CH2:28][O:29][CH3:30])[N:11]=2)[N:13]=1)[NH2:19]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Product 1

HCID 67842295HCID 67842295, compound

Procedure

To a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (3.0 g) and triethylamine (4.7 ml) in N,N-dimethylformamide (60 ml) was added a methoxyacetyl chloride (0.9 ml) under ice-cooling and the mixture was stirred for 2.5 hours at the same temperature. The reaction mixture was added to water and the mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether to give 2-(diaminomethyleneamino)-4-(6-methoxyacetylamino-methylpyridin-2-yl)thiazole (0.86 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  3. washThe extract layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record
ord-f758b99aae494fdb953725771344dd14
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

Loading…