Hydrazinecarboxaldehyde → HCID 86757628, compound

HRID 2268092Notes

Reaction equation

HRID 2268092 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]=[C:25]([CH3:30])[CH:26]=4)[C:21]3=[O:31])[CH2:16][C:17]([OH:19])=[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]=[C:25]([CH3:30])[CH:26]=4)[C:21]3=[O:31])[CH2:16][C:17]3[O:19][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[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1)[N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([CH3:30])[CH:26]=2)[C:21]1=[O:31])=[O:45]

Participants

6

Reactant 3

HCID 12229HydrazinecarboxaldehydeHCID 682631,1'-CarbonyldiimidazoleHCID 12017114HCID 12017114, compound

Product 2

HCID 9911470HCID 9911470, compoundHCID 86757628HCID 86757628, compoundYield 174.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[1-(3-Cyclopentyloxy-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-cyclopentyloxy-4-methoxyphenyl)-3-(5-methyl-1,3-dioxoisoindolin-2-yl)propanoic acid (2.33 g, 5.5 mmol), carbonyidiimidazole (1.07 g, 6.59 mmol) and formic hydrazide (436 mg, 7.26 mmol) in ethyl acetate (20 mL) gave crude N-carbonylamino-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(5-methyl-1,3-dioxoisoindolin-2-yl)propanamide (2.24 g, 4.8 mmol), which was then treated with phosphorus oxychloride (0.9 mL, 9.6 mmol) in acetonitrile (10 mL). The product was obtained as a white solid (728 mg, 32% overall yield): mp, 184.0-186.5° C.; 1H NMR (CDCl3) δ 1.55-2.00 (m, 8H, C5H8), 2.48 (s, 3H, CH3), 3.81 (s, 3H, CH3), 3.82 (dd, J=6.1, 15.7 Hz, 1H, CHH), 4.36 (dd, J=10.3, 15.7 Hz, 1H, CHH), 4.74-4.81 (m, 1H, OCH), 5.79 (dd, J=5.9, 10.3 Hz, 1H, NCH), 6.80 (d, J=8.4 Hz, 1H, Ar), 7.10 (dd, J=2.0, 8.3 Hz, 1H, Ar), 7.18 (d, J=2.0 Hz, 1H, Ar), 7.47 (d, J=7.5 Hz, 1H, Ar), 7.59 (s, 1H, Ar), 7.67 (d, J=7.6 Hz, 1H, Ar), 8.28 (s, 1H, CH); 13C NMR (CDCl3) δ 21.95, 24.09, 27.75, 32.77, 51.79, 56.00, 80.48, 111.73, 114.51, 120.16, 123.34, 123.95, 129.05, 130.22, 132.03, 134.65, 145.44, 147.75, 150.03, 153.00, 164.08, 167.98, 168.11; Anal Calcd for C25H25N3O5+0.13 Et2O: C, 67.05; H, 5.80; N, 9.19. Found: C, 66.95; H, 5.88; N, 8.97. (HNMR showed the sample contained 0.13 equiv. of ether).

Sources & evidence

ORD record
ord-13d1642200b54b6ba422a7997dc620cb
Source dataset
uspto-grants-2001_12
Patent number
US06326388B1

Reaction notes

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