Hydrochloric Acid → HCID 135895256, compound

HRID 1428832Notes

Reaction equation

HRID 1428832 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:35])=[C:16]([S:22]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=4)(=[O:24])=[O:23])[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.C1COCC1.[OH-].[K+].Cl>O>[Cl:35][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][C:16]=1[S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 136337163HCID 136337163, compound

Product 1

HCID 135895256HCID 135895256, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[7-Chloro-6-(3,4-dimethoxy-benzenesulfonyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester was combined with THF (5 mL), followed by the addition of a solution of aqueous 1M KOH (2.7 mL, 2.7 mmol), and the mixture was stirred for 16 h. The reaction mixture was cooled in an ice bath, then 1M aqueous HCl (5 mL) and water (5 mL) was added. The resulting precipitate was collected and purified by HPLC to furnish the titled compound (16 mg, 12%). MS (Cl): mass calcd. for C20H15ClN4O7S, 490.0; m/z found, 489.0 [M−H]−. 1H NMR (500 MHz, DMSO-d6): 13.10 (s, 2H), 8.95 (s, 1H), 8.86 (s, 1H), 8.32 (s, 1H), 7.87 (s, 1H), 7.59 (dd, J=8.6, 1.8, 1H), 7.41 (d, J=2.0, 1H), 7.19 (d, J=8.6, 1H), 3.85 (s, 3H), 3.81 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customThe resulting precipitate was collected
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-a07bfb9c289449b9a601391010f2727e
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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