Benzylamine → N-benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine

HRID 1496634Notes

Reaction equation

HRID 1496634 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:5]=[CH:4][N:3]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([NH:29][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:5]=[CH:4][N:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 866431432-Chloro-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine

Product 1

HCID 67537630N-benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine

Conditions

Temperature
180 °C

Procedure

With stirring, a mixture of 5.24 g (16.4 mmol) of 2-chloro-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine and 25 ml benzylamine is heated at 180° C. After 16 h, the reaction mixture is concentrated under reduced pressure, the residue is taken up in 100 ml of MTBE, the resulting precipitate is filtered off and the filtrate is concentrated again. The residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 4.75 g (88%) of the desired product; 1H-NMR(MeCN-d3) δ: 7.91 (d, 1H), 7.49 (m, 2H), 7.29 (m, 5H), 7.07 (m, 2H), 6.45 (d, 1H), 6.39 (s, 1H), 5.83 (br.s, 1H), 4.43 (d, 2H), 3.02 (q, 2H), 1.38 (t, 3H).

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. filtrationthe resulting precipitate is filtered off
  3. concentrationthe filtrate is concentrated again
  4. customThe residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-6de36ca9f3f64dcf995d7a78c74a89df
Source dataset
uspto-grants-2015_12
Patent number
US09198426B2

Reaction notes

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