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

HRID 595461Notes

Reaction equation

HRID 595461 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1bd8dd0f67da4878bd3d5ac3ba620c42
Source dataset
uspto-grants-2016_01
Patent number
US09242976B2

Reaction notes

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