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Hydrochloric Acid → n-[2,4-Dioxo-6-(tetrahydro-furan-2-yl)-7-trifluoromethyl-1,4-dihydro-2h-quinazolin-3-yl]-methanesulfonamide

HRID 1894034
Notes
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Reaction equation

HRID 1894034 reaction equation
CO[C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH2:19].CC[N:23]([CH2:26]C)CC.[CH3:28][S:29]([NH:32]N)(=[O:31])=[O:30].[OH-:34].[Na+].Cl>C1COCC1>[O:34]=[C:26]1[N:23]([NH:32][S:29]([CH3:28])(=[O:31])=[O:30])[C:3](=[O:20])[C:4]2[C:5](=[CH:6][C:7]([C:15]([F:16])([F:17])[F:18])=[C:8]([CH:10]3[CH2:14][CH2:13][CH2:12][O:11]3)[CH:9]=2)[NH:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 269268MethanesulfonohydrazideHCID 119654552-Amino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 11965456
n-[2,4-Dioxo-6-(tetrahydro-furan-2-yl)-7-trifluoromethyl-1,4-dihydro-2h-quinazolin-3-yl]-methanesulfonamide
Yield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-amino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester (2 g, 6.91 mmol) in anhydrous THF (30 mL) was treated with (CCl3O)2CO (684 mg, 2.28 mmol). The resultant yellow solution was stirred at r.t. for 15 min and Et3N (967 uL, 6.91 mmol) was then added. A thick suspension developed that was diluted with anhydrous THF (20 mL). The suspension was stirred for 3 h at r.t. CH3SO2NHNH2 (777 mg, 6.91 mmol) was added and the reaction was stirred for 1 h. The reaction mixture was then treated with aq NaOH (1 N, 14 mL, 14 mmol) and the resultant orange-red solution was stirred for 1 h at r.t. The reaction mixture was acidified to pH 3-4 with aq HCl (4 N) and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was taken into DCM and triturated. The colorless suspension was collected by vacuum filtration and further dried in vacuo at 60° C. to give the title product (2.36 g, 87%) as colorless crystals. m.p.: 254-257° C., API-ES: m/z 394 [M+H].

Workup

  1. stirringThe suspension was stirred for 3 h at r.t
  2. stirringthe reaction was stirred for 1 h
  3. stirringthe resultant orange-red solution was stirred for 1 h at r.t
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customtriturated
  9. filtrationThe colorless suspension was collected by vacuum filtration
  10. customfurther dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-abb3392b5666493a9db0f64501908434
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08513268B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes