2-Butanamine, 2-methyl- → 3-(1,1-Dimethyl-propylamino)-4-[(5-nitro-benzofuran-2-ylmethyl)-amino]-cyclobut-3-ene-1,2-dione

HRID 363002Notes

Reaction equation

C(O[C:6]1[C:7](=[O:25])[C:8](=[O:24])[C:9]=1[NH:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=2[CH:16]=1)CCC.[C:26]([NH2:31])([CH2:29][CH3:30])([CH3:28])[CH3:27]>C(O)C>[CH3:27][C:26]([NH:31][C:6]1[C:7](=[O:25])[C:8](=[O:24])[C:9]=1[NH:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=2[CH:16]=1)([CH3:28])[CH2:29][CH3:30]

Participants

Conditions

Temperature: 70 °C

Procedure

To 3-butoxy-4-[(5-nitro-benzofuran-2-ylmethyl)-amino]-cyclobut-3-ene-1,2-dione (0.25 g, 0.727 mmol), as prepared in Example 8, in ethanol (5 mL) was added tert-amylamine (0.53 mL, 4.54 mmol). The reaction was stirred at 70° C. for 18 hours and then at room temperature for 48 hours. The precipitated product was filtered and washed with ethyl acetate, diethyl ether, and petroleum ether to afford 0.22 g (85%) of 3-(1,1-dimethyl-propylamino)-4-[(5-nitro-benzofuran-2-ylmethyl)-amino]-cyclobut-3-ene-1,2-dione as an off-white solid: mp 283.5°-287.5° C. (dec); 1H NMR (DMSO-d6): δ 8.61 (d, 1H), 8.18 (dd, 1H), 7.96 (br t, 1H), 7.81 (d, 1H), 7.46 (br s, 1H), 7.07 (s, 1H), 4.99 (d, 2H), 1.66 (q, 2H), 1.30 (s, 6H), 0.82 (t, 3H). IR (KBr): 3220, 2950, 1800 cm-1 ; MS (m/z) 357 (M+).

Workup

waitat room temperature for 48 hours
filtrationThe precipitated product was filtered
washwashed with ethyl acetate, diethyl ether, and petroleum ether

Sources & evidence

ORD record: ord-2beec56e034c4ccabd12a2387c9ecbad
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872139

Reaction notes

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