Hydrochloric Acid → HCID 135895266, compound

HRID 1428835Notes

Reaction equation

HRID 1428835 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:30])[NH:15][C:16]([N:20]4[CH:24]=[C:23]([C:25]([O:27]CC)=[O:26])[CH:22]=[N:21]4)=[N:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].Cl>C1COCC1>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:30])[NH:15][C:16]([N:20]4[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[CH:22]=[N:21]4)=[N:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 136337166HCID 136337166, compound

Product 1

HCID 135895266HCID 135895266, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-(7-benzenesulfonyl-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid, ethyl ester (50 mg, 0.12 mmol), THF (2 mL) and aqueous 1M LiOH (0.6 mL, 0.6 mmol) was stirred for 16 h. The THF was removed under reduced pressure and aqueous 1M HCl (3 mL, 3 mmol) was added. The crude product was collected by filtration and purified by HPLC to afford the titled compound (7.0 mg, 14%). MS (ESI): mass calcd. for C18H12N4O5S, 396.1; m/z found, 397.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.43-12.81 (m, 2H), 8.99 (s, 1H), 8.34-8.25 (m, 2H), 8.18 (s, 1H), 8.05 (d, J=7.6, 2H), 7.96 (dd, J=8.3, 1.5, 1H), 7.78-7.71 (m, 1H), 7.71-7.63 (m, 2H).

Workup

  1. additionwas added
  2. filtrationThe crude product was collected by filtration
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-83023aac98b14b0480593f0ac2536ee4
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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