1,1'-Carbonyldiimidazole → HCID 59242074, compound

HRID 1876153Notes

Reaction equation

[CH3:1][N:2]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:20])[N:11]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[NH:21]([C:23]([O:25][CH3:26])=[O:24])[NH2:22].[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28]>C1COCC1.CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[CH3:1][N:2]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:20])[N:11]=1)[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:27]([NH:22][NH:21][C:23]([O:25][CH3:26])=[O:24])=[O:28])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a mixture of N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine 0.396 g (1.5 mmol) in THF 10 mL and DMF 3 mL was added methyl hydrazine carboxylate 0.135 g (1.5 mmol), followed by addition of carbonyldiimidazole (CDI) 0.243 g (1.5 mmol) at 23° C. The reaction mixture was stirred at 23° C. for 4 h, heated under reflux for 0.5 h, and then stirred at 23° C. for another 16 h. After removal of THF, the crude product was purified with gradient column chromatography (EtOAc/hexanes, 0% to 100%) to give the titled compound in 75% yield, which was used without further purification. 1H NMR (CD3OD, 400 MHz): δ 7.98 (s, 1H), 7.64 (d, 1H, J=8.4 Hz), 7.59-7.54 (m, 1H), 7.52 (d, 2H, J=8.3 Hz), 7.13 (d, 2H, J=8.6 Hz), 7.05 (d, 1H, J=7.2 Hz), 7.03-6.98 (m, 1H), 3.74 (s, 3H), 3.70 (s, 1H), 2.99 (s, 3H), 2.86 (s, 3H). m/e: 381.19 (M+1), 379.03 (M−1).

Workup

temperatureheated
temperatureunder reflux for 0.5 h
stirringstirred at 23° C. for another 16 h
customAfter removal of THF
customthe crude product was purified with gradient column chromatography (EtOAc/hexanes, 0% to 100%)

Sources & evidence

ORD record: ord-40d2ca9325c143119e9d5e41ab6e017c
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

Loading…