Hydrazinecarboxaldehyde → HCID 86757625, compound

HRID 2268089Notes

Reaction equation

HRID 2268089 reaction equation
[O:1]=[C:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[C:4](=[O:15])[N:3]1[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=1)[CH2:17][C:18](O)=[O:19].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:44]([NH:46][NH2:47])=[O:45]>O1CCCC1>[CH2:30]([O:29][C:23]1[CH:22]=[C:21]([CH:16]([N:3]2[C:2](=[O:1])[C:10]3[C:9]4[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=4[CH:7]=[CH:6][C:5]=3[C:4]2=[O:15])[CH2:17][C:18]2[O:19][CH:44]=[N:46][N:47]=2)[CH:26]=[CH:25][C:24]=1[O:27][CH3:28])[CH3:31].[O:1]=[C:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[C:4](=[O:15])[N:3]1[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][CH3:31])[CH:22]=1)[CH2:17][C:18]([NH:47][N:46]=[C:44]=[O:45])=[O:19]

Participants

6

Reactant 3

HCID 12229HydrazinecarboxaldehydeHCID 682631,1'-CarbonyldiimidazoleHCID 12017111HCID 12017111, compound

Product 2

HCID 12017113HCID 12017113, compoundHCID 86757625HCID 86757625, compoundYield 122.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[1-(3-Ethoxy-4-methoxyphenyl)-2-(1,3,4-oxadiazol-2-yl)ethyl]benzo[e]isoindoline-1,3-dione was prepared by the procedure used in Example 1. Thus, reaction of 3-(1,3-dioxobenzo[e]isoindolin-2-yl)-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (1.50 g, 3.58 mmol), carbonyidiimidazole (0.70 g, 4.3 mmol) and formic hydrazide (310 mg, 5.16 mmol) in tetrahydrofuran (20 mL) gave crude 3-(1,3-dioxobenzo[e]isoindolin-2-yl)-N-carbonylamino-3-(3-ethoxy4-methoxyphenyl)propanamide (1.0 g, 2.2 mmol), which was then treated with phosphorus oxychloride (POCl3, 0.4 mL, 4.3 mmol) in acetonitrile (10 mL). The product was obtained as a yellow solid (135 mg, 8% overall yield): mp, 139.0-141.5° C.; 1H NMR (CDCl3) δ 1.47 (t, J=7.2 Hz, 3H, CH3), 3.85 (s, 3H, CH3), 3.87 (dd, J=6.0, 15.6 Hz, 1H, CHH), 4.13 (q, J=6.9 Hz, 2H, CH2), 4.42 (dd, J=10.2, 15.6 Hz, 1H, CHH), 5.87 (t, J=5.9, 10.4 Hz, 1H, NCH), 6.84 (d, J=8.7 Hz, 1H, Ar), 7.18-7.27 (m, 2H, Ar), 7.64-7.75 (m, 2H, Ar), 7.81 (d, J=8.3 Hz, 1H, Ar), 7.94 (d, J=7.6 Hz, 1H, Ar), 8.14 (d, J=8.2 Hz, 1H, Ar), 8.29 (s, 1H, CH), 8.90 (d, J=7.5 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.63, 27.79, 51.69, 55.84, 64.39, 111.34, 112.53, 118.41, 121.22, 124.83, 126.88, 127.93, 128.62, 128.74, 129.44, 130.31, 130.87, 135.06, 136.59, 148.37, 149.36, 152.95, 164.04,168.51, 169.07; Anal Calcd for C25H21N3O5: C, 67.71; H, 4.77; N, 9.48. Found: C, 67.80; H, 4.95; N, 9.20.

Sources & evidence

ORD record
ord-c612a97261404465a888ae6edbac5d39
Source dataset
uspto-grants-2001_12
Patent number
US06326388B1

Reaction notes

Loading…