Hydrochloric Acid → HCID 67228750, compound

HRID 448372Notes

Reaction equation

HRID 448372 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[C:14](=[O:30])[N:15]([CH:22]2[CH2:27][CH2:26][C:25](=[O:28])[NH:24][C:23]2=[O:29])[C:16]3=[O:21])=[C:7]([O:31][CH3:32])[CH:6]=1)[CH3:3].[ClH:33]>C(Cl)Cl.CO.CCOCC>[ClH:33].[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[C:14](=[O:30])[N:15]([CH:22]2[CH2:27][CH2:26][C:25](=[O:28])[NH:24][C:23]2=[O:29])[C:16]3=[O:21])=[C:7]([O:31][CH3:32])[CH:6]=1)[CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58827255HCID 58827255, compound

Product 1

HCID 67228750HCID 67228750, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

4-(4-Dimethylaminomethyl-2-methoxyphenylamino)-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione (0.42 g, 1.0 mmol) was dissolved in 9:1 methylene chloride-methanol (75 mL) and a 2 M solution of hydrogen chloride in ether (1.0 mL) was added. The mixture was stirred at room temperature for 1 hour, and was evaporated under vacuum. The residue was triturated with ether and filtered, providing 0.44 g, in quantitative yield: mp>260° C.; 1H NMR (DMSO-d6) δ 1.96-2.14 (m, 1H), 2.53-2.68 (m, 8H), 2.84-2.95 (m, 1H), 3.90 (s, 3H), 4.24 (s, 2H), 5.13 (d, J=7.8 Hz, 1H), 7.13 (d, J=7.1 Hz, 1H), 7.28 (d, J=5.7 Hz, 1H), 7.25-7.66 (m, 4H), 8.41 (s, 1H), 11.11 (br, 1H), 11.14 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 41.4, 48.8, 56.1, 59.4, 112.3, 113.7, 114.3, 119.3, 123.5, 126.1, 129.0, 132.2, 136.4, 141.7, 150.0, 167.0, 168.8, 170.0, 172.8; Anal. calcd for C23H25ClN4O5.0.5H2O.0.1Et2O: C, 57.44; H, 5.56; N, 11.45. Found: C, 57.44; H, 5.48; N, 11.08.

Workup

  1. customwas evaporated under vacuum
  2. customThe residue was triturated with ether
  3. filtrationfiltered
  4. customproviding 0.44 g

Sources & evidence

ORD record
ord-10addb9e3d244992936f7d561051d079
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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