Tetrahydrofuran → 1-(5-Tert-butyl-2-(1-(2-(dimethylamino)ethyl)-3,3-dimethyl-2-oxopiperazine-4-carbonyl)thiophen-3-yl)-3-(2,3-dichlorophenyl)urea

HRID 18924Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:23]([CH3:26])([CH3:25])[CH3:24])[S:5][C:6]=1[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:11](=[O:20])[C:10]1([CH3:22])[CH3:21])=[O:8].[Cl:27][C:28]1[C:29]([Cl:37])=[C:30]([N:34]=[C:35]=[O:36])[CH:31]=[CH:32][CH:33]=1.C1COCC1>C(OCC)(=O)C>[C:23]([C:4]1[S:5][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])[C:11](=[O:20])[C:10]2([CH3:21])[CH3:22])=[O:8])=[C:2]([NH:1][C:35]([NH:34][C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([Cl:27])[C:29]=2[Cl:37])=[O:36])[CH:3]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 4-(4-amino-2-tert-butylthiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one (0.035 g, 0.092 mmol), dichlorophenyl isocyanate (0.019 g, 0.10 mmol), and THF (2 mL) was heated at 75° C. for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, dried, the solvent eliminated under vacuum and the crude product was purified by preparative thin layer chromatography (dichloromethane:methanol, 95:5) to afford 0.035 g of 1-(5-tert-butyl-2-(1-(2-(dimethylamino)ethyl)-3,3-dimethyl-2-oxopiperazine-4-carbonyl)thiophen-3-yl)-3-(2,3-dichlorophenyl)urea. 1H NMR (400 MHz, acetone-d6): δ (ppm) 9.57 (bs, 1H); 8.86 (bs, 1H); 8.17 (d, 1H); 7.65 (s, 1H); 7.30 (m, 2H); 3.90 (m, 2H); 3.60 (m, 2H); 3.50 (t, 2H); 2.43 (t, 2H); 2.20 (s, 6H); 1.70 (s, 6H); 1.40 (s, 9H).

Workup

washwashed with saturated sodium bicarbonate
customdried
customthe crude product was purified by preparative thin layer chromatography (dichloromethane:methanol, 95:5)

Sources & evidence

ORD record: ord-9d86c46e42b3410b98ab25d58e8b0204
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741479B2

Reaction notes

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