N-(3-(2,6-dioxopiperidin-3-yl)-2-methyl-4-oxo-3,4-dihydroquinazolin-5-yl)formamide → Avadomide

HRID 1777232Notes

Reaction equation

HRID 1777232 reaction equation
[H][H].[O:3]=[C:4]1[CH:9]([N:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:21]C=O)[N:12]=[C:11]2[CH3:24])[CH2:8][CH2:7][C:6](=[O:25])[NH:5]1>C(O)=O>[NH2:21][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:19](=[O:20])[N:10]([CH:9]1[CH2:8][CH2:7][C:6](=[O:25])[NH:5][C:4]1=[O:3])[C:11]([CH3:24])=[N:12]2

Participants

4

Reactant 2

HCID 90000864N-(3-(2,6-dioxopiperidin-3-yl)-2-methyl-4-oxo-3,4-dihydroquinazolin-5-yl)formamideHCID 178418361HCID 178418361, compound

Product 1

HCID 24967599Avadomide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In certain embodiments, when the hydrogen donor is formic acid, the transfer hydrogenation further comprises the step of hydrolyzing N-(3-(2,6-dioxopiperidin-3-yl)-2-methyl-4-oxo-3,4-dihydroquinazolin-5-yl)formamide to form 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione as described herein elsewhere.

Sources & evidence

ORD record
ord-d25fb31a0435468797157c2cb6e3280d
Source dataset
uspto-grants-2016_02
Patent number
US09266858B2

Reaction notes

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