Triethylamine → 2-(Diaminomethyleneamino)-4-[6-(furfurylthio)acetylaminomethylpyridin-2-yl)thiazole

HRID 1491857Notes

Reaction equation

HRID 1491857 reaction equation
Cl.Cl.Cl.[NH2:4][CH2:5][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.C(N(CC)CC)C.[CH2:28]([S:34][CH2:35][C:36](O)=[O:37])[C:29]1[O:33][CH:32]=[CH:31][CH:30]=1.CN(C)CCCN=C=NCC>CN(C)C=O.O.C(OCC)(=O)C>[NH2:19][C:18](=[N:17][C:14]1[S:15][CH:16]=[C:12]([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:5][NH:4][C:36](=[O:37])[CH2:35][S:34][CH2:28][C:29]3[O:33][CH:32]=[CH:31][CH:30]=3)[N:11]=2)[N:13]=1)[NH2:20]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3021476(Furfurylthio)acetic acidHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Product 1

HCID 103410612-(Diaminomethyleneamino)-4-[6-(furfurylthio)acetylaminomethylpyridin-2-yl)thiazoleYield 43.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.5 g), triethylamine (1.8 ml), (furfurylthio)acetic acid (0.8 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.0 g) in N,N-dimethylformamide (15 ml) was stirred at ambient temperature for 18 hours. The mixture was added to a mixture of ethyl acetate and water and the separated organic layer was dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether to give 2-(diaminomethyleneamino)-4-[6-(furfurylthio)acetylaminomethylpyridin-2-yl)thiazole (0.73 g).

Workup

  1. dry with materialthe separated organic layer was dried over magnesium sulfate
  2. customEvaporation of the solvent
  3. customgave a residue, which
  4. customwas purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V)
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record
ord-c7f80b4ecbc64b249333d9b83a4c1dc5
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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