Lithium Hydroxide → 6-(Benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinic acid

HRID 595461노트

반응식

HRID 595461 반응식
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[CH:21]=[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])[C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][N:12]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li+].[OH-]>C(O)C.O>[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[CH:21]=[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 89689730Ethyl 6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinate

생성물 1

HCID 896896766-(Benzo[d]thiazol-6-ylamino)-4-(isopropylamino)nicotinic acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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).

후처리

  1. temperaturethe then heated at 70° C. for 1 h
  2. concentrationThe solvent was concentrated under reduced pressure
  3. additiondiluted with EtOAc
  4. additionadded water
  5. customThe aqueous layer was collected
  6. customSolid material precipitated out
  7. filtrationFiltered the solid material
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-1bd8dd0f67da4878bd3d5ac3ba620c42
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242976B2

반응 노트

불러오는 중…