Potassium Hydroxide → {5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acid potassium salt

HRID 82108Notes

Reaction equation

HRID 82108 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[C:14]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[N:22]([CH2:29][C:30]([O:32]C)=[O:31])[CH:21]=3)=[O:19])[CH:15]=[N:16][CH:17]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[K+:35]>CO>[K+:35].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:13]=[C:14]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[N:22]([CH2:29][C:30]([O-:32])=[O:31])[CH:21]=3)=[O:19])[CH:15]=[N:16][CH:17]=2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 70847670Methyl {5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetate

Product 1

HCID 70817542{5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetic acid potassium saltYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of methyl {5-[(5-{[(4-chlorophenyl)acetyl]amino}pyridin-3-yl)carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}acetate (Example 306, 197 mg, 0.425 mmol) in MeOH (4 mL) was added an aqueous solution of KOH (0.425 mL of a 1M solution, 0.425 mmol) and then further MeOH (4 mL) was added. The reaction was stirred for 2 hours at room temperature. The reaction was concentrated in vacuo to give the title compound as a light brown solid in 99% yield, 205 mg.

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-2ff96448bbaa438e969adab9ac33117b
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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