Water → HCID 66699722, compound

HRID 1014727Notes

Reaction equation

[C:1]1([C@H:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][CH:20]=[N:21]4)[N:13]=[CH:12][C:11]=2[NH2:26])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[C:28](N)=[O:29].O>CN1CCCC1=O>[C:1]1([C@H:7]([N:9]2[C:10]3[CH:15]=[C:14]([C:16]4[CH:25]=[CH:24][CH:23]=[C:22]5[C:17]=4[CH:18]=[CH:19][CH:20]=[N:21]5)[N:13]=[CH:12][C:11]=3[NH:26][C:28]2=[O:29])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 185 °C

Procedure

1-((1R)-1-phenylethyl)-6-(5-quinolyl)-4-imidazolino[4,5-c]pyridine-2-one. ((1R)-1-Phenylethyl)(3-amino-6-(5-quinolyl)(4-pyridyl))amine (150 mg, 0.44 mmol) and urea (52.8 mg, 0.88 mmol) were combined in 1-methylpyrrolidin-2-one (4 mL) and heated at 185° C. for 2 h. Water (10 mL) was added and the crude product was collected by filtration. The product was purified by reverse-phase preparative HPLC (20-95% acetonitrile in water, over 30 min) to give the title compound (52.3 mg, 32.4%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.45 (s, 1H) 8.91 (dd, J=4.10, 1.56, 1H) 8.39 (d, J=0.78, 1H) 8.33 (ddd, J=8.74, 1.71, 0.88, 1H) 8.05 (d, J=8.49, 1H) 7.80 (dd, J=8.49, 7.13, 1H) 7.59 (dd, J=7.22, 1.37, 1H) 7.41-7.46 (m, 3H) 7.30-7.40 (m, 3H), 5.75 (d, J=7.22, 1H), 4.16 (d, J=0.98, 1H), 1.87 (d, J=7.22, 3H); MS (ESI) m/z 367.0 [M+1]+.

Workup

filtrationthe crude product was collected by filtration
customThe product was purified by reverse-phase preparative HPLC (20-95% acetonitrile in water, over 30 min)

Sources & evidence

ORD record: ord-1f9b4b061d8e494a8af11ad341d5e8ec
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981893B2

Reaction notes

Loading…