2,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamide → N-hydroxy-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxamide

HRID 1616124Notes

Reaction equation

HRID 1616124 reaction equation
[O:1]=[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([C:13]([NH:15][O:16]C3CCCCO3)=[O:14])=[CH:7][CH:8]=2)[NH:3]1>C1COCC1.C(O)(=O)C.O>[OH:16][NH:15][C:13]([C:6]1[CH:5]=[C:4]2[C:9]([C:10](=[O:12])[NH:11][C:2](=[O:1])[NH:3]2)=[CH:8][CH:7]=1)=[O:14]

Participants

5

Reactant 1

HCID 866642012,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamide

Product 1

HCID 86664202N-hydroxy-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxamideYield 44.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamide (0.12 g, 0.39 mmol) in THF (1.6 mL), acetic acid (3.2 mL) and water (0.8 mL) was heated at 60° C. for 5 h. The mixture was concentrated to dryness. The residue was purified by preparative HPLC to afford N-hydroxy-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxamide (38 mg, 44%). LC-MS: (FA) ES+ 222; 1H NMR (400 MHz, DMSO) δ 11.42 (s, 1H), 11.40 (s, 1H), 11.28 (s, 1H), 9.21 (d, J=1.6 Hz, 1H), 7.92 (d, J=8.2 Hz, 1H), 7.52 (s, 1H), 7.44 (dd, J=8.2, 1.3 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-fbe4f929a0f24a3ba09e0aa5db55f012
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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