Hydrochloric Acid → 4-[(4-aminopiperidin-1-yl)carbonyl]-N-(2-fluoro-4-iodophenyl)pyridin-3-amine

HRID 39549Notes

Reaction equation

HRID 39549 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:30])[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])[CH2:10][CH2:9]1)(C)(C)C.Cl>C(O)(C(F)(F)F)=O.ClCCl.CO.C(OCC)C>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])=[O:30])[CH2:10][CH2:9]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 11497541Tert-butyl(1-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}piperidin-4-yl)carbamate2×

Product 1

HCID 116478704-[(4-aminopiperidin-1-yl)carbonyl]-N-(2-fluoro-4-iodophenyl)pyridin-3-amine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent2×

Procedure

4-[(4-aminopiperidin-1-yl)carbonyl]-N-(2-fluoro-4-iodophenyl)pyridin-3-amine was synthesized from tert-butyl(1-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}piperidin-4-yl)carbamate (described below) by deprotection of the Boc group with TFA/DCM: 0.33 mmol of tert-butyl(1-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}piperidin-4-yl)carbamate was dissolved in 4 ml of 50:50 mixture of TFA/dichloromethane. After 2 hours of stirring at room temperature the volatiles were stripped and the residue was re-dissolved in 2 ml of methanol. 1.0N HCl in diethylether was added and the product precipitated. LC/MS [2.01 min; 441 (free base, M+1)]

Workup

  1. customthe product precipitated
  2. customLC/MS [2.01 min; 441 (free base, M+1)]

Sources & evidence

ORD record
ord-3174d3d0689448b89db7b0967b0e897d
Source dataset
uspto-grants-2013_09
Patent number
US08524911B2

Reaction notes

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