Dimethylformamide → HCID 10318301, compound

HRID 1033067Notes

Reaction equation

HRID 1033067 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)=[CH:5][CH:4]=1.[CH2:17]([CH2:23][C:24](O)=[S:25])[C:18]1OC=CC=1.Cl.[CH3:28]N(C)CCCN=C=NCC.[C:39](=[O:42])([O-])[O-].[K+].[K+].CN(C)[CH:47]=[O:48]>O.O1CCCC1.C(OCC)(=O)C>[NH2:15][C:14](=[N:13][C:10]1[S:11][CH:12]=[C:8]([C:6]2[O:7][C:3]([CH2:2][NH:1][C:39](=[O:42])[CH2:28][S:25][CH2:24][C:23]3[O:48][CH:47]=[CH:18][CH:17]=3)=[CH:4][CH:5]=2)[N:9]=1)[NH2:16]

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103992684-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazoleHCID 178526176HCID 178526176, compound

Product 1

HCID 10318301HCID 10318301, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (4.0 g), furfurylthioacetic acid (3.4 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.2 g) in N,N-dimethylformamide (40 ml) was stirred for 15 hours at ambient temperature. The mixture was added a mixture of ethyl acetate, tetrahydrofuran and water and the mixture was adjusted to pH 9.5 with potassium carbonate. The separated organic layer was washed with a brine and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate 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 isopropyl ether to give 2-(diaminomethyleneamino)-4-[5-{(furan-2-yl)methylthio}acetamidomethylfuran-2-yl]thiazole (3.50 g).

Workup

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

Sources & evidence

ORD record
ord-45c6cff0c4b045d3b828377f51e67724
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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