Sodium Hydroxide → 2-((1-(Tert-butoxycarbonyl)piperidin-4-yl)amino)isonicotinic acid

HRID 2202083Notes

Reaction equation

HRID 2202083 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][N:24]=2)[C:18]([O:20]C)=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][N:24]=2)[C:18]([OH:20])=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90238214Methyl 2-((1-(tert-butoxycarbonyl)piperidin-4-yl)amino)isonicotinate

Product 1

HCID 902380262-((1-(Tert-butoxycarbonyl)piperidin-4-yl)amino)isonicotinic acidYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-((1-(tert-butoxycarbonyl)piperidin-4-yl)amino)isonicotinate (230 g, 0.69 mol) in MeOH (1500 mL) was added aq.NaOH (56 g, in 200 mL of water) over 20 min at 0° C. After addition, the mixture was stirred at room temperature for 2 h. MeOH was then removed under reduced pressure and the aqueous solution then pH adjusted to pH=6 by acidifying with the addition of 4N HCl. The resulting precipitate was collected by filtration, washed with water and dried to give the crude product. Three batches were run in parallel and produced a combined crude product weight of 590 g, yield: 89.4%. This crude was used in next step without further purification. LCMS (m/z): 322.2 (M+1).

Workup

  1. additionAfter addition
  2. customMeOH was then removed under reduced pressure
  3. additionby acidifying with the addition of 4N HCl
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried
  7. customto give the crude product

Sources & evidence

ORD record
ord-56c283ccd54447919e52c3b460d9cf15
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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