Potassium Hydroxide → 1-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid

HRID 384666Notes

Reaction equation

HRID 384666 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)[C:13]([N:31]3[CH:35]=[CH:34][C:33]([C:36]([O:38]CC)=[O:37])=[CH:32]3)=[CH:12][N:11]=2)=[N:7][CH:8]=1)#[N:2].[OH-].[K+]>C(O)C>[C:27]([O:26][C:24]([N:20]1[CH2:21][CH2:22][CH2:23][CH:18]([CH2:17][NH:16][C:14]2[CH:15]=[C:10]([NH:9][C:6]3[CH:5]=[N:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[N:11]=[CH:12][C:13]=2[N:31]2[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32]2)[CH2:19]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 71022175tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-(ethoxycarbonyl)-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 667465061-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-(ethoxycarbonyl)-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (42 mg, 0.077 mmol) was dissolved in ethanol (1 mL). KOH (43 mg, 0.770 mmol) was added and the solution was stirred at 50° C. for 72 h. The reaction mixture was evaporated to dryness and the residue was partitioned between water and dichloromethane. The two phases were separated and the organic phase was extracted with water. The combined aqueous phases were neutralised to pH 7 by the addition of 1M HCl and then evaporated to dryness. The product (7 mg, 17%) was used directly in the next step without further purification.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was partitioned between water and dichloromethane
  3. customThe two phases were separated
  4. extractionthe organic phase was extracted with water
  5. additionThe combined aqueous phases were neutralised to pH 7 by the addition of 1M HCl
  6. customevaporated to dryness
  7. customThe product (7 mg, 17%) was used directly in the next step without further purification

Sources & evidence

ORD record
ord-b2fad7ed8ae347e48b79b1ef49a37dc8
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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