Potassium Carbonate → (4-Chloro-2-pyridin-3-yl-thiazol-5-yl)-methylamine

HRID 533299Notes

Reaction equation

HRID 533299 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[S:5][C:6]=1[N:7](C)[C:8](=O)C(F)(F)F.C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[N:3]=[C:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[S:5][C:6]=1[NH:7][CH3:8]

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 59580860N-(4-Chloro-2-pyridin-3-yl-thiazol-5-yl)-2,2,2-trifluoro-N-methyl-acetamide

Product 1

HCID 59580506(4-Chloro-2-pyridin-3-yl-thiazol-5-yl)-methylamineYield 86.4%

Procedure

A solution of N-(4-chloro-2-pyridin-3-yl-thiazol-5-yl)-2,2,2-trifluoro-N-methyl-acetamide (0.337 g, 1 mmol) in ice-cold methanol (18 mL) was treated with potassium carbonate (0.434 g, 3.1 mmol) and stirred under nitrogen for 20 min. The solids were removed by filtration, and the filtrate was concentrated under reduced pressure and it was adsorbed onto silica gel. Purification by silica gel chromatography eluting with a gradient of ethyl acetate in hexanes afforded a bright yellow solid (0.195 g, 82%): mp 79° C. (dec); 1H NMR (400 MHz, CDCl3) δ 8.97 (d, J=2.1 Hz, 1H), 8.55 (dd, J=4.8, J=1.5 Hz, 1H), 8.08 (ddd, J=8.1, 2.0, 2.0 Hz, 1H), 7.32 (dd, J=8.1, 4.8 Hz, 1H), 4.07 (br m, 1H), 3.03 (d, J=5.3 Hz, 3H); ESIMS m/z 228.23 (M+2); IR 1540 cm−1.

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure and it
  3. customPurification by silica gel chromatography
  4. washeluting with a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1a9758f9d0e44871ad6632b954a39953
Source dataset
uspto-grants-2014_10
Patent number
US08853246B2

Reaction notes

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