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

HRID 1803416Notes

Reaction equation

HRID 1803416 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-9da0c175e76d43fbba829798559279ee
Source dataset
uspto-grants-2013_01
Patent number
US08350044B2

Reaction notes

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