Methanol → HCID 11750453, compound

HRID 2354189Notes

Reaction equation

HRID 2354189 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:38])=[C:11]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH:25]5[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.CO>Cl.O1CCOCC1>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:8]=[CH:9][C:10]([CH3:38])=[C:11]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:12]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 887MethanolHCID 66918946HCID 66918946, compound

Product 1

HCID 11750453HCID 11750453, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-[(3-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-4-oxo-3,4-dihydroquinazolin-6-yl)oxy]piperidine-1-carboxylate (3.42 g) was stirred in 4N HCl in dioxane (20 ml) and methanol (3 ml) at room temperature for 18 hours and then concentrated. The residue was purified by column chromatography on an ion exchange column (isolute SCX-2 column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) washing with methanol initially and then eluting with a 99:1 mixture of methanol and aqueous ammonia solution to give N-cyclopropyl-4-methyl-3-[4-oxo-6-(piperidin-4-yloxy)quinazolin-3(4H)-yl]benzamide (2.67 g) as a light brown solid; NMR Spectrum: (DMSOd6) 0.54 (m, 2H), 0.69 (m, 2H), 1.50 (m, 2H), 1.95 (m, 2H), 2.15 (s, 3H), 2.60 (m, 2H), 2.85 (m, 1H), 2.95 (m, 2H), 4.59 (m, 1H), 7.51 (d, 1H), 7.52 (d, 1H), 7.59 (s, 1H), 7.71 (d, 1H), 7.82 (s, 1H), 7.90 (d, 1H), 8.18 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 419.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on an ion exchange column (isolute SCX-2 column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  3. washwashing with methanol initially
  4. washeluting with a 99:1 mixture of methanol and aqueous ammonia solution

Sources & evidence

ORD record
ord-a842463dfb2343c3bc8fa506a22aeae1
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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