Acetic Acid → HCID 68730412, compound

HRID 509465Notes

Reaction equation

HRID 509465 reaction equation
[Br:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9]C(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=O.Cl.[NH2:15][CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:17]1=[O:23].C(N(CC)CC)C.C(O)(=O)C>C(#N)C>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=1[C:7]([NH:15][CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:17]1=[O:23])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 2885615-Bromoisatoic Anhydride

Product 1

HCID 68730412HCID 68730412, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 5-bromo-isatoic anhydride (6.0 g, 25 mmol), 3-amino-piperidine-2,6-dione hydrogen chloride (4.1 g, 25 mmol), triethylamine (18 mL, 129 mmol), and acetic acid (15 mL, 262 mmol) in acetonitrile (60 mL) was heated at 90° C. for 18 hours. The suspension was filtered and washed with acetonitrile (2×80 mL), water (2×80 mL) and ethyl acetate (2×80 mL) to give 2-amino-N-(2,6-dioxo-piperidin-3-yl)-5-bromo-benzamide as a white solid (5.8 g, 72% yield): LCMS: MH=326, 328. The sample was used in the next step without further purification.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with acetonitrile (2×80 mL), water (2×80 mL) and ethyl acetate (2×80 mL)

Sources & evidence

ORD record
ord-03bb780c10cd4e9b9869e17865ffd4c0
Source dataset
uspto-grants-2015_08
Patent number
US09096573B2

Reaction notes

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