Acetic Acid → HCID 18975331, compound

HRID 2393445Notes

Reaction equation

HRID 2393445 reaction equation
C(OC(=O)C=[CH:6][C:7]1[C:15]2[C:10](=[CH:11][N:12]=[C:13]([N:16]3[CH:20]=[N:19]C=N3)[CH:14]=2)[NH:9][CH:8]=1)C.C1N2CN3[CH2:31][N:25](C2)CN1C3.C(O)(=[O:34])C>>[CH:6]([C:7]1[C:15]2[C:10](=[CH:11][N:12]=[C:13]([N:16]3[CH:20]=[N:19][N:25]=[CH:31]3)[CH:14]=2)[NH:9][CH:8]=1)=[O:34]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 67655264HCID 67655264, compound

Product 1

HCID 18975331HCID 18975331, compoundYield 38%

Procedure

A mixture of Intermediate 5 (1.62 g, 8.7 mmol) and hexamethylenetetramine (1.47 g, 10.5 mmol) was refluxed in 33% aqueous acetic acid (10 mL) for 75 min. The mixture was cooled in ice for 2 hours and the precipitate was collected by filtration to give the title compound (0.71 g, 38%) as a beige solid. The filtrate was evaporated and the residue chromatographed on silica eluting with 10% MeOH in DCM to give the title compound (0.39 g, 21%) (overall yield 59%), as a yellow solid. mp 155° C. (dec.). 1H NMR (360 MHz, d6 -DMSO) δ 8.35 (1H, s), 8.68 (1H, s), 8.83 (1H, s), 9.30 (2H, s), 10.05 (1H, s) and 12.74 (1H, br s).

Workup

  1. temperatureThe mixture was cooled in ice for 2 hours
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2c654cfcf44144a8b06c71531e077597
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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