Hydrochloric Acid → HCID 11965456, compound

HRID 906530Notes

Reaction equation

HRID 906530 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

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 269268MethanesulfonohydrazideHCID 11965455HCID 11965455, compound

Product 1

HCID 11965456HCID 11965456, compoundYield 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 μL, 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-1250fd54fc3f4bf09b06d643bd720211
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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