Dimethylformamide → HCID 131718228, compound

HRID 1656446Notes

Reaction equation

Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=N.C[N:14](C=O)C.[C:18]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19]1>CN(C1C=CC=CN=1)C.N1C=CC=CC=1>[NH2:14][N:9]=[CH:7][C:6]1[CH:5]=[C:4]([NH:3][CH:21]([CH:22]=[O:23])[CH2:20][CH2:19][C:18]([OH:24])=[O:25])[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Aminobenzamidine di-HCL (5 g, 24 mmol) was added to dry DMF (30 mL). To this solution dry pyridine (5 mL) and glutaric anhydride (3.0 g, 26 mmol), followed by 10 mg dimethylaminopyridine (DMAP) were added. The product was heated for 3 h at 100° C. and allowed to stir at room temperature for 16 h. Solvents were removed in vacuo, water was added to the residue and the pH was brought to a value of 6.8 using dilute sodium hydroxide. An abundant precipitate was filtered, washed with water followed by ethyl acetate. The white solid was filtered and dried in a desiccator to give 5.4 g, 90% of product as a white solid: 1H NMR (d6 -DMSO) δ 1.8 (m, 2H), 2.3 (m, 2H), 2.45 (m, 2H), 7.6 (d, 1H, J=8 Hz), 7.55 (dd, 1H, J=8 Hz and J= 7.5 Hz), 7.85 (d, 1H, J=7.5 Hz), 8.05 (s, 1H), 9.05 (bs, 2H), 9.25 (bs, 2H), 10.4 (s, 1H); MS (FAB) m/e 250.1 (MH+).

Workup

additionwere added
customSolvents were removed in vacuo, water
additionwas added to the residue
filtrationAn abundant precipitate was filtered
washwashed with water
filtrationThe white solid was filtered
customdried in a desiccator

Sources & evidence

ORD record: ord-7ee2fe3b36b54da783dc9ea5a6ff82c6
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254573

Reaction notes

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