Hydrazinecarboxaldehyde → HCID 86757629, compound

HRID 2268093Notes

Reaction equation

HRID 2268093 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([N:20]3[C:28](=[O:29])[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[CH3:30])[C:21]3=[O:31])[CH2:16][C:17](O)=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:44]([NH:46][NH2:47])=[O:45]>C(OCC)(=O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([N:20]3[C:28](=[O:29])[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[CH3:30])[C:21]3=[O:31])[CH2:16][C:17]3[O:18][CH:44]=[N:46][N:47]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1.[C:44](=[N:46][NH:47][C:17](=[O:18])[CH2:16][CH:15]([C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1)[N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[CH3:30])[C:21]1=[O:31])=[O:45]

Participants

6

Reactant 3

HCID 12229HydrazinecarboxaldehydeHCID 682631,1'-CarbonyldiimidazoleHCID 12017116HCID 12017116, compound

Product 2

HCID 12017118HCID 12017118, compoundHCID 86757629HCID 86757629, compoundYield 139.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-(1,3,4-oxadiazol-2-yl)ethyl]-4-methylisoindoline-1,3-dione was prepared by the procedure of Example 1. Reaction of 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(4-methyl-1,3-dioxoisoindolin-2-yl)propanoic acid (2.23 g, 5.27 mmol), carbonyldiimidazole (0.94 g, 5.8 mmol) and formic hydrazide (382 mg, 6.36 mmol) in ethyl acetate (20 mL) gave crude N-carbonylamino-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(4-methyl-1,3-dioxoisoindolin-2-yl)propanamide (1.71 g, 3.67 mmol), which was then treated with phosphorus oxychloride (0.8 mL, 8.6 mmol) in acetonitrile (10 mL). The product was obtained as a white solid (368 mg, 16% overall yield): mp, 126.0-128.5° C.; 1H NMR (CDCl3) δ 1.21-1.99 (m, 8H, C5H8), 2.66 (s, 3H, CH3), 3.81 (s, 3H, CH3), 3.82 (dd, J=6.1, 15.8 Hz, 1H, CHH), 4.37 (dd, J=10.3, 15.6 Hz,1H, CHH), 4.76-4.83 (m,1H, OCH), 5.80 (dd, J=5.9, 10.3 Hz, 1H, NCH), 6.81 (d, J=8.4 Hz, 1H, Ar), 7.09-7.18 (m, 2H, Ar), 7.43 (d, J=7.6 Hz, 1H, Ar), 7.54 (t, J=7.4 Hz, 1H, Ar), 7.62 (d, J=7.1 Hz, 1H, Ar), 8.29 (s, 1H, CH); 13C NMR (CDCl3) δ 17.45, 24.00, 27.67, 32.68, 51.57, 55.94, 80.44, 111.69, 114.55, 120.13, 120.98, 128.25, 130.22, 132.01, 133.50, 136.44, 138.08, 147.68, 149.99, 152.93, 164.04, 167.95, 168.56; Anal Calcd for C25H25N3O5: C, 67.10; H, 5.63; N, 9.39. Found: C, 67.14; H, 5.55; N, 9.19.

Sources & evidence

ORD record
ord-730a7f8ac9c14375ba740b7fa25047ba
Source dataset
uspto-grants-2001_12
Patent number
US06326388B1

Reaction notes

Loading…