Trifluoroacetic acid → (6-Methoxy-4-oxo-7-(piperidin-4-ylmethoxy)quinazolin-3(4H)-yl)methyl pivalate

HRID 577370Notes

Reaction equation

HRID 577370 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20](=[O:34])[N:21]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[CH:22]=[N:23]3)=[CH:18][C:17]=2[O:35][CH3:36])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:36][O:35][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:16]=1[O:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[N:23]=[CH:22][N:21]([CH2:26][O:27][C:28](=[O:33])[C:29]([CH3:30])([CH3:31])[CH3:32])[C:20]2=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11733854tert-Butyl 4-(((6-methoxy-4-oxo-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylate

Product 1

HCID 11058522(6-Methoxy-4-oxo-7-(piperidin-4-ylmethoxy)quinazolin-3(4H)-yl)methyl pivalateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.32 g, 4.6 mmol) in methylene chloride (23 ml) containing TFA (5 ml) was stirred at ambient temperature for 1 hour. The volatiles were removed under vacuum. The residue was partitioned between ethyl acetate and sodium hydrogen carbonate. The organic solvent was removed under vacuum and the residue was filtered. The precipitate was washed with water, and dried under vacuum. The solid was azeotroped with toluene and dried under vacuum to give 6-methoxy-7-(piperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.7 g, 92%).

Workup

  1. customThe volatiles were removed under vacuum
  2. customThe residue was partitioned between ethyl acetate and sodium hydrogen carbonate
  3. customThe organic solvent was removed under vacuum
  4. filtrationthe residue was filtered
  5. washThe precipitate was washed with water
  6. customdried under vacuum
  7. customThe solid was azeotroped with toluene
  8. customdried under vacuum

Sources & evidence

ORD record
ord-dfea5019c8a243d3a3521699b66565a1
Source dataset
uspto-grants-2015_05
Patent number
US09040548B2

Reaction notes

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