4-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amine → (4-Mesitylthiazol-2-yl)(pyridin-4-yl)methanone

HRID 1484712Notes

Reaction equation

HRID 1484712 reaction equation
[C:1]1([CH3:15])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:10]=[C:11](N)[S:12][CH:13]=1.Cl.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]1([CH3:15])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:9]1[N:10]=[C:11]([C:17]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[O:24])[S:12][CH:13]=1

Participants

5

Reactant 2

HCID 6127164-(2,4,6-Trimethylphenyl)-1,3-thiazol-2-amineHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 118006174(4-Mesitylthiazol-2-yl)(pyridin-4-yl)methanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 4-mesitylthiazol-2-amine (7.8 g, 37 mmol)4 in CH2Cl2 (200 mL) was added DMAP (9.0 g, 74 mmol) followed by isonicotinoyl chloride hydrochloride (8.5 g, 48 mmol). Then the mixture was stirred at room temperature for 2 hr. After that, the concentrated mixture was subjected to purification by silica gel chromatography followed by recrystallization from ethanol to give INH41 (10.2 g, 85%) as a white solid; mp 202-203° C. 1H NMR (400 MHz, CDCl3) δ 12.71 (br, 1H), 8.65 (dd, 2H, J=1.6, 4.8 Hz), 7.47 (dd, 2H, J=1.6, 4.8 Hz), 6.79 (s, 1H), 6.54 (s, 2H), 2.15 (s, 3H), 1.87 (s, 6H). 13C NMR (100.5 MHz, CDCl3) δ 164.0, 159.4, 150.2, 148.4, 138.7, 138.0, 136.8, 130.8, 128.5, 121.2, 112.3, 21.1, 20.4. MS (ESI) m/z 324.1 (M+H+), 346.1 (M+Na+). HRMS calculated. for C18H18N3OS (M+H+): 324.1171. found: 324.1167; calculated. for C18H17N3OSNa (M+Na+): 346.0990. found: 346.0984.

Workup

  1. customAfter that, the concentrated mixture was subjected to purification by silica gel chromatography
  2. customfollowed by recrystallization from ethanol
  3. customto give INH41 (10.2 g, 85%) as a white solid

Sources & evidence

ORD record
ord-b8e41d44e9b44b569ebaa05b478c2e7c
Source dataset
uspto-grants-2016_08
Patent number
US09422275B2

Reaction notes

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