Ammonium formate → N-{[3-(3,4-Dimethoxybenzyl)-2,4-dioxo-1-(piperidin-4-yl)-1,2,3,4-tetrahydroquinazolin-6-yl]methyl}acetamide

HRID 403570Notes

Reaction equation

HRID 403570 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH:16]1[CH2:21][CH2:20][N:19](C(OCC3C=CC=CC=3)=O)[CH2:18][CH2:17]1)[C:11](=[O:32])[N:10]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH3:43])[CH:35]=1)[C:9]2=[O:44])(=[O:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:43][O:42][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][C:37]=1[O:40][CH3:41])[CH2:33][N:10]1[C:9](=[O:44])[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:7]=2)[N:12]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:11]1=[O:32]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66603329Benzyl 4-{6-[(acetylamino)methyl]-3-(3,4-dimethoxybenzyl)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}piperidine-1-carboxylate

Product 1

HCID 66603539N-{[3-(3,4-Dimethoxybenzyl)-2,4-dioxo-1-(piperidin-4-yl)-1,2,3,4-tetrahydroquinazolin-6-yl]methyl}acetamideYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.1 g of benzyl 4-{6-[(acetylamino)methyl]-3-(3,4-dimethoxybenzyl)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}piperidine-1-carboxylate obtained in stage 5.6, 0.016 g of ammonium formate and 0.018 g of Pd/C (10%) in 2 ml of EtOH purged beforehand with nitrogen is irradiated under a microwave field at 800° C. for 30 min. The mixture is filtered and the filtrate is evaporated under reduced pressure to give 0.077 g of the expected product.

Workup

  1. customis irradiated under a microwave field at 800° C. for 30 min
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-6bc3ea9648414ec1b88743a29a6c46f1
Source dataset
uspto-grants-2014_06
Patent number
US08748441B2

Reaction notes

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