Ethyl Acetate → HCID 68603925, compound

HRID 641985Notes

Reaction equation

HRID 641985 reaction equation
C1(N[C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][C@H:25]5[CH2:29][CH2:28][NH:27][CH2:26]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)CC1.C(OCC)(=[O:33])C>Br>[CH3:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]([OH:33])=[O:30])=[CH:7][C:8]=1[N:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][C@H:25]3[CH2:29][CH2:28][NH:27][CH2:26]3)[CH:20]=2)[N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 11338653HCID 11338653, compound

Product 1

HCID 68603925HCID 68603925, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of N-Cyclopropyl-4-methyl-3-[4-oxo-6-[(3S)-pyrrolidin-3-yloxy]quinazolin-3(4H)-yl]benzamide (0.5 g) in 48% hydrobromic acid (5 ml) was heated to 130° C. for 30 minutes in a microwave (Personal Chemistry Emrys Optimizer with 300 W magnetron). The reaction mixture was diluted with ethyl acetate and extracted with water. The aqueous extracts were combined and purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to give 4-methyl-3-[4-oxo-6-[(3S)-pyrrolidin-3-yloxy]quinazolin-3(4H)-yl]benzoic acid as a solid (224 mg); NMR Spectrum: (DMSOd6) 2.13 (m, 7H), 3.30 (m, 2H), 4.89 (s, 1H), 5.26 (s, 1H), 7.45 (m, 2H), 7.58 (t, 1H), 7.70 (d, 1H), 7.80 (s, 1H), 7.92 (m, 1H), 8.15 (s, 1H); Mass Spectrum: M+H+ 366.

Workup

  1. extractionextracted with water
  2. custompurified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  3. additiona 99:1 mixture of methanol and aqueous ammonia solution

Sources & evidence

ORD record
ord-6522061db8d84044914edf359ca1bdce
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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