Trifluoroacetic acid → Benzyl 4-[6-(aminomethyl)-3-(3,4-dimethoxybenzyl)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carboxylate

HRID 80482Notes

Reaction equation

HRID 80482 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[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(OC(C)(C)C)=O)[CH:14]=2)[N:9]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])[CH2:29][CH2:28]2)[C:8]1=[O:43].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:19][CH2:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[O:34])[CH2:29][CH2:28]1)[C:8](=[O:43])[N:7]([CH2:6][C:5]1[CH:44]=[CH:45][C:46]([O:47][CH3:48])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:16]2=[O:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66603765HCID 66603765, compound

Product 1

HCID 59587267Benzyl 4-[6-(aminomethyl)-3-(3,4-dimethoxybenzyl)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carboxylateYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.102 g of benzyl 4-[3-(3,4-dimethoxybenzyl)-6-({[(1,1-dimethylethoxy)carbonyl]amino}methyl)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carboxylate obtained in stage 5.4 and 0.5 ml of TFA in 9.5 ml of DCM is stirred at AT for 2 h 00. A saturated NaHCO3 solution is added. The organic phase is dried over Na2SO4 and filtered, and the filtrate is evaporated under reduced pressure to give 0.09 g of the expected product.

Workup

  1. dry with materialThe organic phase is dried over Na2SO4
  2. filtrationfiltered
  3. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-4b5dd781d1a246aa81f4409c6bd078a5
Source dataset
uspto-grants-2014_09
Patent number
US08846654B2

Reaction notes

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