반응 #964710

반응 방정식

Ethyl 6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinate

ethyl 6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinate

LiOH

→

title compound ( 4 )

6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinic acid

용매

ethanol

water

반응 조건

후처리

1. 1
   온도the then heated at 70° C. for 1 h
2. 2
   농축The solvent was concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with EtOAc
4. 4
   workup.ADDITIONadded water
5. 5
   기타The aqueous layer was collected
6. 6
   기타Solid material precipitated out
7. 7
   여과Filtered the solid material
8. 8
   기타dried under vacuum

실험 절차

Ethyl 6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinate (3) (1 g, 2.8 mmol) in ethanol (20 mL) and water (5 mL) was stirred at rt then added LiOH (14 mmol, 5 equiv.). The reaction mixture was stirred at room temperature for 4 h, the then heated at 70° C. for 1 h. The solvent was concentrated under reduced pressure, diluted with EtOAc and added water. The aqueous layer was collected and acidified to pH 3-4 using solid citric acid. Solid material precipitated out. Filtered the solid material and dried under vacuum to furnish the title compound (4). LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 0.65 min; LCMS (ES-API), m/z 329.8 (M+H).

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