Acetic Anhydride → HCID 69247967, compound

HRID 1525822Notes

Reaction equation

HRID 1525822 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C1COCC1.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16](=[O:36])[N:17]([CH:24]1[CH2:29][CH2:28][C:27](=[O:30])[N:26]([CH2:31][CH2:32][O:33][CH3:34])[C:25]1=[O:35])[C:18]2=[O:23]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:34][O:33][CH2:32][CH2:31][N:26]1[C:27](=[O:30])[CH2:28][CH2:29][CH:24]([N:17]2[C:18](=[O:23])[C:19]3[C:15](=[C:14]([NH:13][C:1](=[O:3])[CH3:2])[CH:22]=[CH:21][CH:20]=3)[C:16]2=[O:36])[C:25]1=[O:35]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 69247466HCID 69247466, compound

Product 1

HCID 69247967HCID 69247967, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.5 mL) and DMAP (3 mg) were added to a THF solution of 4-amino-2-(1-(2-methoxyethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (50 mg). The reaction mixture was allowed to react for 8 hrs at room temperature. Then, DCM (15 mL) were added and solvents were removed by rotary evaporation in vacuo. The residue was washed with 0.5 N aqueous hydrochloric acid, saturated sodium bicarbonate, and brine, dried over anhydrous magnesium sulfate, and filtered. Pale white solid (38 mg) was obtained after removal of solvent by rotary evaporation in vacuo. MS (m/e): 374 (M+H).

Workup

  1. customto react for 8 hrs at room temperature
  2. customsolvents were removed by rotary evaporation in vacuo
  3. washThe residue was washed with 0.5 N aqueous hydrochloric acid, saturated sodium bicarbonate, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-8cff6ef190584b2fadc3a70da78fba29
Source dataset
uspto-grants-2015_07
Patent number
US09085563B2

Reaction notes

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