Ammonium formate → HCID 25253199, compound

HRID 403571Notes

Reaction equation

HRID 403571 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[CH:14]=2)[N:9]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:8]1=[O:29].[CH:35]([O-])=[O:36].[NH4+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[CH:14]=2)[N:9]([CH:23]2[CH2:28][CH2:27][N:26]([CH:35]=[O:36])[CH2:25][CH2:24]2)[C:8]1=[O:29]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 66603539N-{[3-(3,4-Dimethoxybenzyl)-2,4-dioxo-1-(piperidin-4-yl)-1,2,3,4-tetrahydroquinazolin-6-yl]methyl}acetamide

Product 1

HCID 25253199HCID 25253199, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.070 g of N-{[3-(3,4-dimethoxybenzyl)-2,4-dioxo-1-(piperidin-4-yl)-1,2,3,4-tetrahydroquinazolin-6-yl]methyl}acetamide obtained in stage 5.7 and 0.028 g of ammonium formate in 2 ml of ACN is irradiated under a microwave field at 140° C. for 1 h 00. The mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an MeOH/DCM mixture, (0.5/99.5, v/v) as far as (7/93, v/v), to give 0.035 g of the expected product.

Workup

  1. customis irradiated under a microwave field at 140° C. for 1 h 00
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-5f0aeaf80f4944149c4ef44488ccc4a7
Source dataset
uspto-grants-2014_06
Patent number
US08748441B2

Reaction notes

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