Water → 1-(2-Phenylcyclopropyl)-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazin-3-YL}urea

HRID 2424490Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethyl-phenyl)methanone (123 mg, 0.35 mmol) in DMF (20.0 mL) was added (2-isocyanatocyclopropyl)benzene (111 mg, 0.7 mmol). The mixture was stirred at 60° C. overnight. After cooling, the mixture was poured into water (120 mL). The white solid, which precipitated, was filtered off and dried in vacuum to give the title product (162 mg) as a white solid in 90% yield. 1H NMR (300 MHz, CDCl3) δ 8.01-7.97, 7.73, 7.60, 7.55, 7.32, 7.22-7.10, 7.06, 4.00-3.95, 3.87-3.86, 3.62-3.52, 3.43-3.41, 3.25-3.22, 2.85-2.82, 2.14-2.10, 0.91-0.86. MS (ES+) m/z 511.2 (M+1).

Workup

temperatureAfter cooling
customThe white solid, which precipitated
filtrationwas filtered off
customdried in vacuum

Sources & evidence

ORD record: ord-4d3cfee2f95e4b6da520c6e5e0d8a952
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964591B2

Reaction notes

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