Lithium Hydroxide → HCID 135895284, compound

HRID 1428813Notes

Reaction equation

HRID 1428813 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:20][C:19](=[O:21])[C:18]3[C:13](=[CH:14][C:15]([Cl:22])=[CH:16][CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[Li+].[OH-]>C1COCC1>[Cl:22][C:15]1[CH:14]=[C:13]2[C:18]([C:19](=[O:21])[NH:20][C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 136337156HCID 136337156, compound

Product 1

HCID 135895284HCID 135895284, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-(7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (240 mg, 0.74 mmol), 1M aq. LiOH (4.0 mL), and THF (6 mL) was rapidly stirred for 6 h. The mixture was concentrated to remove the THF, and the aqueous residue was cooled to 0° C. and acidified to pH 2 with 1 M aq. HCl. The resulting precipitate was collected by filtration to provide the titled compound (205 mg, 71%). MS (Cl): mass calcd. for C12H7ClN4O3, 290.7; m/z found, 289.0 [M−H]−. 1H NMR (400 MHz, DMSO-d6): 12.99 (br s, 2H), 8.93 (d, J=0.7 Hz, 1H), 8.27 (s, 1H), 8.11 (d, J=8.5 Hz, 1H), 7.74 (d, J=1.9 Hz, 1H), 7.54 (dd, J=8.5, 2.1 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the THF
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f6d5d4c2182e49fd911b40e68d9d7829
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

Loading…