Ethyl Acetate → HCID 86747907, compound

HRID 1109061Notes

Reaction equation

[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]NCCCCCCC)[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38](S(C1C=CC(C)=CC=1)(=O)=O)[C:39]([NH2:41])=[O:40].C(O[CH2:56][CH3:57])(=O)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH:19]([CH2:56][CH3:57])[CH2:20][CH2:21][CH2:22][CH2:23][NH:41][C:39]([NH:38][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=3)=[O:40])[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (4.35 g; 0.01 mol) and pyridyltosylurea (3.2 g; 0.011 mol; Frigola Conatansa, Jordi; ES 534,782) in diphenyl ether (35 mLs) was stirred under nitrogen at 180° C. for 30 minutes. The cooled solution was chromatographed with 1:1 hexane:ethyl acetate to give the title compound (4.03 g; 0.0073 mol) as an orange oil. 1H NMR (CDCl3) δ 8.15-8.05(m, 1H), 7.9(d, 1H, J=8.4 Hz), 7.6-7.4(m, 5H), 7.3-7.1 (m, 8H), 6.9-6.8 (m, 1H), 3.32 (t, 2H, J=7.2 Hz), 3.25(t,2H, J=7.9 Hz), 3.05(t,2H, J=6.6 Hz), 1.8-1.45(m,8H), 1.4-1.2(m, 8H), 0.9(t,3H, J=6.8 Hz).

Workup

customThe cooled solution was chromatographed with 1:1 hexane

Sources & evidence

ORD record: ord-2df9b240320f4e0fa5356a82eed3a934
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05318984

Reaction notes

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