1,1'-Carbonyldiimidazole → HCID 9950577, compound

HRID 9844Notes

Reaction equation

HRID 9844 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:16]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:25])[CH2:12][C:13](O)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:39][OH:40]>O1CCCC1>[OH:40][NH:39][C:13](=[O:14])[CH2:12][CH:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[N:16]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:25]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 35695923-(3,4-dimethoxyphenyl)-3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid

Product 1

HCID 9950577HCID 9950577, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Hydroxy-3-(3,4-dimethoxyphenyl)-3-(1-oxoisoindolinyl)propionamide was prepared by the procedure of Example 1 from 3-(3,4-dimethoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (5.00 g, 14.7 mmol), carbonyldiimidazole (2.49 g, 15.4 mmol) and hydroxylamine hydrochloride (1.30 g, 19.1 mmol) in tetrahydrofuran (15 mL) to afford N-hydroxy-3-(3,4-dimethoxyphenyl)-3-(1-oxoisoindolinyl)propionamide as a white solid (4.1 g, 79% yield): mp, 188.5–189.5° C.; 1H NMR (DMSO-d6) δ 2.82–2.87 (m, 2H, CH2), 3.71 (s, 3H, CH3), 3.74 (s, 3H, CH3), 4.15 (d, J=17.5 Hz, NCHH), 4.63 (d, J=17.5 Hz, 1H, NCHH), 5.74 (t, J=7.7 Hz, 1H, NCH), 6.85–6.93 (m, 3H, Ar), 7.45–7.69 (m, 4H, Ar), 8.83 (br s, 1H, OH), 10.60 (1H, NH); 13C NMR (DMSO-d6) δ 35.11, 46.26, 51.25, 55.50, 111.09, 111.76, 119.19, 122.79, 123.43, 127.84, 131.29, 131.91, 132.27, 141.68, 148.27, 148.69, 166.03, 166.84; Anal Calcd for C19H20N2O5: C, 64.04; H, 5.66; N, 7.86. -Found: C, 64.08; H, 5.55; N, 7.86.

Sources & evidence

ORD record
ord-909a3d25a3a2447daf56d1285f6de8cb
Source dataset
uspto-grants-2006_08
Patent number
US07091356B2

Reaction notes

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