3-Aminophthalic acid → 4-amino-2-(2-oxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 718717Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[C:11]([OH:13])=O.[NH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:21]>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]2[C:3]=1[C:11](=[O:13])[N:14]([CH:15]1[CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:21])[C:5]2=[O:7]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-aminophthalic acid (0.100 g, 0.552 mmol) in DMF (1.1 mL) was added 3-aminopiperidine-2-one (0.063 g, 0.552 mmol) and the reaction was stirred at 90° C. over 18 h. Volatiles were removed in vacuo and the dark-brown crude residue was purified by preparative reverse phase HPLC to give the desired product 28 (0.050 g, 35%) as an off-white powder. 1H NMR (400 MHz, DMSO) δ 7.83 (s, 1H), 7.43 (dd, J=8.3, 7.1 Hz, 1H), 7.07-6.87 (m, 2H), 6.47 (br s, 2H), 4.49 (dd, J=11.9, 6.3 Hz, 1H), 3.27-3.10 (m, 2H), 2.19 (dt, J=12.0, 7.7 Hz, 1H), 2.05-1.72 (m, 3H). MS (ESI) m/z calcd for C13H14N3O3 [M+H]+ 260.3, found: 260.9.

Workup

customVolatiles were removed in vacuo
customthe dark-brown crude residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-049fff498c564f37b6548b05bb0d0ab3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193989B2

Reaction notes

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