Methyl 4-((tert-butoxycarbonyl)amino)nicotinate → Methyl 4-aminopyridine-3-carboxylate

HRID 1823681Notes

Reaction equation

HRID 1823681 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10]C(OC(C)(C)C)=O)=[CH:8][CH:7]=[N:6][CH:5]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 1

HCID 23438729Methyl 4-((tert-butoxycarbonyl)amino)nicotinate

Product 1

HCID 592353Methyl 4-aminopyridine-3-carboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Formula 505 where R1, R3 and R4 are H; W, Y and Z are —C═; and X is —N═: 4-tert-Butoxycarbonylamino-nicotinic acid methyl ester (9.08 g, 36.0 mmol) was dissolved in 50/50 TFA/DCM (100 mL) solution and stirred for 2 hours at room temperature. Concentration of the mixture under reduced pressure was followed by re-dissolution in DCM (100 mL), washing with saturated sodium bicarbonate, drying over sodium sulfate, and concentration under reduced pressure. The corresponding de-protected product of Formula 505, 4-amino-nicotinic acid methyl ester (5.43 g, 99.1%) was obtained was obtained in sufficient purity to be carried forward for use in the next step. MS (Cl) M/E: 153.1.

Workup

  1. washwashing with saturated sodium bicarbonate
  2. dry with materialdrying over sodium sulfate, and concentration under reduced pressure

Sources & evidence

ORD record
ord-eca684a786ca46be89b55d6f4167d7f2
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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