Hydrochloric Acid → HCID 23577846, compound

HRID 1827456Notes

Reaction equation

HRID 1827456 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]([C:26](=[O:29])[NH:27][CH3:28])=[N:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:13][CH:12]=1.[OH-].[Na+].Cl.CCOC(C)=O>CO.O1CCCC1.O>[CH3:28][NH:27][C:26]([C:15]1[C:14]2[C:18](=[CH:19][C:11]([NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:30])=[O:2])=[CH:12][CH:13]=2)[N:17]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[N:16]=1)=[O:29]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 23577857HCID 23577857, compound

Product 1

HCID 23577846HCID 23577846, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-Methylcarbamoyl-1-(tetrahydro-pyran-2-yl)-1H-indazol-6-ylamino]-benzoic acid methyl ester (0.20 g, 0.49 mmol) in methanol (1.4 mL) and tetrahydrofuran (0.6 mL) was added a solution of sodium hydroxide (59 mg, 1.47 mmol) in water (0.3 mL). The reaction was heated to 60 degrees Celsius for 1 hour and then was cooled to room temperature. The pH was adjusted with 2 N HCl to a pH of 2. EtOAc (30 mL) and water (30 mL) was added and the layers were separated. The aqueous was extracted with EtOAc (3×20 mL) and the organic layers were combined. After washing with water (15 mL), the organic layer was dried over Na2SO4. The solids were filtered away, and the organic was evaporated to yield a yellow solid (193 mg, 100%).

Workup

  1. temperatureThe reaction was heated to 60 degrees Celsius for 1 hour
  2. customthe layers were separated
  3. extractionThe aqueous was extracted with EtOAc (3×20 mL)
  4. washAfter washing with water (15 mL)
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationThe solids were filtered away
  7. customthe organic was evaporated

Sources & evidence

ORD record
ord-9250925820754bb8984ae49cf9fae8ca
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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