Diisopropylethylamine → 3,3,9,9-Tetramethyl-1-(4-methyl-2-nitro-1H-imidazol-1-yl)-4,8-diazaundecane-2,10-dione dioxime

HRID 278387Notes

Reaction equation

Cl[C:2]([CH3:17])([CH3:16])[CH:3]([N:14]=[O:15])[CH2:4][N:5]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]1[N+:11]([O-:13])=[O:12].[NH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([CH3:30])([CH3:29])[C:24](=[N:27][OH:28])[CH2:25]C.CCN(C(C)C)C(C)C>C(#N)C>[CH3:16][C:2]([CH3:17])([NH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([CH3:30])([CH3:29])[C:24](=[N:27][OH:28])[CH3:25])[C:3](=[N:14][OH:15])[CH2:4][N:5]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]1[N+:11]([O-:13])=[O:12]

Participants

Conditions

Temperature: 50 °C

Procedure

3-Chloro-3-methyl-2-nitroso-1-(4-methyl-2-nitro-1H-imidazol-1-yl) butane (3.41 g, 13.09 mmol) was added in portions to a stirred solution of N-(3-aminopropyl)-1-amino-1,1-dimethyl-2-butanone oxime (2.0 g, 11.56 mmol, Example 1) and (i-Pr)2NEt (1.64 g, 13.09 mmol) in dry acetonitrile (20 mL) at 50° C. under a nitrogen atmosphere. After the addition the reaction mixture was stirred for an additional 2 hours at 50° C. and cooled to room temperature. The solid which formed was filtered and recrystallized from acetonitrile to provide the title product as a light yellow colored solid. Yield: 3.08 g (59.4%); mp. 140-141° C.; 1H NMR (DMSO-d6) δ 1.12 & 1.19[2s, 6H, C(CH3)2], 1.33(m, 2H, CH2CH2CH2), 1.70[s, 3H, C(=N)CH3], 1.79 (bs, 2H, NH) 2.15(s, 3H, imi-CH3), 2.19(m, 4H, NHCH2), 5.19[s, 2H, NCH2C(=N)], 7.05 (s, 1H, imi-CH) and 10.33 & 11.36 (2s, 2H, NOH). MS m/e 398 (M+H)+.

Workup

additionAfter the addition the reaction mixture
temperaturecooled to room temperature
customThe solid which formed
filtrationwas filtered
customrecrystallized from acetonitrile

Sources & evidence

ORD record: ord-85a0c010b7dd4985923a1399d5883d8e
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359120B1

Reaction notes

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