Potassium Hydroxide → HCID 121267897, compound

HRID 2205556Notes

Reaction equation

HRID 2205556 reaction equation
[NH2:1][C:2]1[C:11]([C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=4)=[O:23])=[CH:17][C:15]=3[CH:16]=2)=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][N:3]=1.[OH-].[K+]>CO.O>[NH2:1][C:2]1[C:11]([C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=4)=[O:23])=[CH:17][C:15]=3[CH:16]=2)=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 121267854HCID 121267854, compound

Product 1

HCID 121267897HCID 121267897, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

To the stirring mixture of methyl 6-amino-5-[5-({[(3-methylphenyl)amino]carbonyl}amino)-1-benzothien-2-yl]nicotinate (420 mg, 0.972 mmol, 1 eq) in MeOH—H2O (3:1, 20 mL) at room temperature was added potassium hydroxide pellets (272 mg, 5 eq) and the reaction mixture was stirred at 65° C. for total of two hours, at which time the reaction mixture became a clear yellow solution. The solution was concentrated under reduced pressure to remove most part of methanol. The mixture was then cooled in an ice-bath, concentrated hydrochloride was added dropwise, and the pH was adjusted to about 3. After the mixture was stirred for about another 30 minutes, it was filtered through a Buchner funnel, rinsed with water, and 6-amino-5-[5-({[(3-methylphenyl)amino]carbonyl}amino)-1-benzothien-2-yl]nicotinic acid was obtained as a yellow solid in quantitative yield.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customto remove most part of methanol
  3. temperatureThe mixture was then cooled in an ice-bath
  4. additionconcentrated hydrochloride was added dropwise
  5. stirringAfter the mixture was stirred for about another 30 minutes, it
  6. filtrationwas filtered through a Buchner funnel
  7. washrinsed with water

Sources & evidence

ORD record
ord-0c2de453fad64176afdc70eb3f85fe0f
Source dataset
uspto-grants-2016_06
Patent number
US09371314B2

Reaction notes

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