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

HRID 2199193Notes

Reaction equation

HRID 2199193 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-ae3cfc677ad04623b0d8e063a6e63589
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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