Triethylamine → Ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylate

HRID 45403

Reaction equation

HRID 45403 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.C(N(CC)CC)C.Cl.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>O1CCCC1>[C:21]([NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 719362Ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (5.70 g, 30.60 mmol) and triethylamine (10.0 mL, 71.80 mmol) in tetrahydrofuran (100 mL) was added isonicotinoyl chloride hydrochloride (6.00 g, 32.00 mmol). The reaction mixture was stirred at ambient temperature for 2 days. The solvent was removed by evaporation and the resulting white solid was washed sequentially with water, 10% sodium bicarbonate solution, and water, then dried to afford the title compound in 90% yield (8.10 g); 1H NMR (DMSO-d6, 300 MHz) δ 8.77 (d, J=6.0 Hz, 2H), 8.77 (d, J=6.0 Hz, 2H), 4.23 (q, J=7.2 Hz, 2H), 2.34 (s, 3H). 1.27 (t, J=7.2 Hz, 3H); MS (ES+) m/z 292.0 (M+1).

Workup

  1. customThe solvent was removed by evaporation
  2. washthe resulting white solid was washed sequentially with water, 10% sodium bicarbonate solution, and water
  3. customdried

Sources & evidence

ORD record
ord-2a7f7b852a024355ba6a8f13ce27cd05
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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