Sodium Hydroxide → 2-{3-[2-(5-Ethyl-pyridin-2-yl)-vinyl]-1H-indazol-6-ylamino}-benzoic acid

HRID 1827464Notes

Reaction equation

HRID 1827464 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:20]=[CH:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[CH:24][N:23]=3)=[N:16][NH:17]2)=[CH:13][CH:12]=1.[OH-].[Na+].[NH4+].[Cl-]>CO.C1COCC1.O>[CH2:28]([C:25]1[CH:26]=[CH:27][C:22]([CH:21]=[CH:20][C:15]2[C:14]3[C:18](=[CH:19][C:11]([NH:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([OH:30])=[O:2])=[CH:12][CH:13]=3)[NH:17][N:16]=2)=[N:23][CH:24]=1)[CH3:29]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 69354171HCID 69354171, compound

Product 1

HCID 693546052-{3-[2-(5-Ethyl-pyridin-2-yl)-vinyl]-1H-indazol-6-ylamino}-benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{3-[2-(5-Ethyl-pyridin-2-yl)-vinyl]-1H-indazol-6-ylamino}-benzoic acid methyl ester (50 mg, 0.104 mmol) in methanol (0.42 mL) and THF (0.10 mL) was added a solution of sodium hydroxide (12 mg, 0.311 mmol) in water (0.05 mL). The solution was heated to 60 degrees Celsius for 3.5 hours and then neutralized with saturated NH4Cl. The reaction was diluted with water (20 mL), and then extracted with EtOAc (2×20 mL). The combined extracts were first dried over Na2SO4, and then the solids were removed by filtration. The desired product (48.7 mg, 100%) was recovered after rotary evaporation to remove the solvents.

Workup

  1. temperatureThe solution was heated to 60 degrees Celsius for 3.5 hours
  2. extractionextracted with EtOAc (2×20 mL)
  3. dry with materialThe combined extracts were first dried over Na2SO4
  4. customthe solids were removed by filtration
  5. customThe desired product (48.7 mg, 100%) was recovered
  6. customafter rotary evaporation
  7. customto remove the solvents

Sources & evidence

ORD record
ord-091c92d575d94f7fb71eb58683e25efc
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

Loading…