{6-[4-(Methanesulfonylamino-methyl)-phenyl]-pyridin-2-yl}carbamic acid tert-butyl ester → n-(4-(6-Aminopyridin-2-yl)benzyl)methanesulfonamide

HRID 17967Notes

Reaction equation

HRID 17967 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:16][CH:15]=2)[N:9]=1)(C)(C)C>Cl.CO>[NH2:7][C:8]1[N:9]=[C:10]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:19]=2)[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 59165933{6-[4-(Methanesulfonylamino-methyl)-phenyl]-pyridin-2-yl}carbamic acid tert-butyl ester

Product 1

HCID 59166205n-(4-(6-Aminopyridin-2-yl)benzyl)methanesulfonamideYield 94.5%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of {6-[4-(methanesulfonylamino-methyl)-phenyl]-pyridin-2-yl}carbamic acid tert-butyl ester (11 g, 29 mmol) in HCl/MeOH (4M, 300 mL) was stirred at room temperature overnight. The mixture was concentrated to dryness. The residue was filtered and washed with ether to give N-(4-(6-aminopyridin-2-yl)benzyl)methane sulfonamide (C-3) (7.6 g, 80%) 1H NMR (300 MHz, DMSO-d6) δ 14.05 (br s, 1H), 8.24 (br s, 2H), 7.91-7.98 (m, 3H), 7.70 (t, J=6.0 Hz, 1H), 7.53 (d, J=8.1 Hz, 2H), 7.22 (d, J=6.9 Hz, 1H), 6.96 (d, J=9 Hz, 1H), 4.23 (d, J=5.7 Hz, 2H), 2.89 (s, 3H). MS (ESI) m/z (M+H)+: 278.0,

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. filtrationThe residue was filtered
  3. washwashed with ether

Sources & evidence

ORD record
ord-c626474fc884438ba0947cd28f844f56
Source dataset
uspto-grants-2010_06
Patent number
US07741321B2

Reaction notes

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