Hydrazinecarboxaldehyde → HCID 86757627, compound

HRID 2268091Notes

Reaction equation

HRID 2268091 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:27])[CH:23]=3)[C:18]2=[O:28])[CH2:13][C:14](O)=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:41]([NH:43][NH2:44])=[O:42]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH3:27])[CH:23]=3)[C:18]2=[O:28])[CH2:13][C:14]2[O:15][CH:41]=[N:43][N:44]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[C:41](=[N:43][NH:44][C:14](=[O:15])[CH2:13][CH:12]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH3:27])[CH:23]=2)[C:18]1=[O:28])=[O:42]

Participants

6

Reactant 3

HCID 12229HydrazinecarboxaldehydeHCID 682631,1'-CarbonyldiimidazoleHCID 219886643-(3-Ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acid

Product 2

HCID 18349249HCID 18349249, compoundHCID 86757627HCID 86757627, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[1-(3-Ethoxy-4-methoxyphenyl)-2-(1,3,4-oxadiazol-2-yl)ethyl]-5-methylisoindoline-1,3-dione was prepared by the procedure of Example 1. Reaction of 3-(3-ethoxy-4-methoxyphenyl)-3-(5-methyl-1,3-dioxoisoindolin-2-yl)propanoic acid (1.81 g, 4.72 mmol), carbonyldiimidazole (0.92 g, 5.7 mmol) and formic hydrazide (375 mg, 6.2 mmol) in ethyl acetate (20 mL) gave crude N-carbonylamino-3-(3-ethoxy-4-methoxyphenyl)-3-(5-methyl-1,3-dioxoisoindolin-2-yl)propanamide (0.93 g, 2.2 mmol), which was then treated with phosphorus oxychloride (0.4 mL, 4.3 mmol) in acetonitrile (12 mL). The product was obtained as a white solid (371 mg, 19% overall yield): mp, 122.0-124.0° C.; 1H NMR (CDCl3) δ 1.45 (t, J=6.9 Hz, 3H, CH3), 2.48 (s, 3H, CH3), 3.80 (dd, J=6.0, 15.6 Hz, 1H, CHH), 3.84 (s, 3H, CH3), 4.10 (q, J=6.9 Hz, 2H, CH2), 4.35 (dd, J=10.3, 15.6 Hz, 1H, CHH), 5.79 (dd, J=6.0, 10.2 Hz, 1H, NCH), 6.82 (d, J=8.1 Hz, 1H, Ar), 7.12-7.17 (m, 2H, Ar), 7.47 (d, J=7.5 Hz, 1H, Ar), 7.59 (s, 1H, Ar), 7.68 (d, J=7.6 Hz, 1H, Ar), 8.28 (s, 1H, Ar); 13C NMR (CDCl3) δ 14.61, 21.86, 27.67, 51.71, 55.83, 64.36, 111.29, 112.49, 120.22, 123.27, 123.88, 128.97, 130.23, 131.95, 134.58, 145.39, 148.33, 149.34, 152.93, 163.97, 167.91, 168.04; Anal Calcd for C22H21N3O5: C, 64.86; H, 5.20; N, 10.31. Found: C, 64.77; H, 5.07; N, 10.30.

Sources & evidence

ORD record
ord-5f23c511c5814b289b87794be14a1ef2
Source dataset
uspto-grants-2001_12
Patent number
US06326388B1

Reaction notes

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