Triethylamine → HCID 86690877, compound

HRID 1465574Notes

Reaction equation

HRID 1465574 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:22])[C:3]=1[C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1.C(N(CC)CC)C.Cl.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1>C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)[CH:5]=[C:4]([CH3:22])[C:3]=1[C:23]1[N:24]=[C:25]([NH:28][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=2)[S:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86690875HCID 86690875, compound

Product 1

HCID 86690877HCID 86690877, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(2,6-dimethyl-4-(4-phenoxyphenoxy)phenyl)thiazol-2-amine (26-4, 0.500 g, 1.29 mmol) in THF (6.4 mL) was added triethylamine (0.39 g, 3.86 mmol) followed by isonicotinoyl chloride hydrochloride (0.46 g, 2.58 mmol). The reaction mixture was stirred at 60° C. overnight. The solution was concentrated under reduced pressure and added with water. The resultant precipitate was filtered and dried to give N-{4-(2,6-dimethyl-4-(4-phenoxyphenoxy)phenyl)thiazol-2-yl}isonicotinamide (26, 0.51 g) as light yellow solids in 80% yield: 1H NMR (500 MHz, CDCl3) δ 8.72 (m, 2 H), 7.61 (m, 2 H), 7.31-7.34 (m, 2 H), 7.08-7.10 (m, 1 H), 6.94-7.02 (m, 6 H), 6.80 (s, 1H), 6.49 (s, 2 H), 1.94 (s, 6 H). ESI-MS: m/z 494.2 (M+H)+.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionadded with water
  3. filtrationThe resultant precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-13535f81735b401fa3e417cffdcf9e5e
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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