Triethylamine → HCID 86690861, compound

HRID 1465556Notes

Reaction equation

HRID 1465556 reaction equation
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([C:17]3[N:18]=[C:19]([NH2:22])[S:20][CH:21]=3)=[C:12]([CH3:23])[CH:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1>C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([C:17]3[N:18]=[C:19]([NH:22][C:34](=[O:41])[C:35]4[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=4)[S:20][CH:21]=3)=[C:12]([CH3:23])[CH:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86690859HCID 86690859, compound

Product 1

HCID 86690861HCID 86690861, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(4-isopropoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-amine (16-6, 0.25 g, 0.72 mmol) in CH2Cl2 (5.0 mL) was added triethylamine (0.5 mL, 3.59 mmol) followed by isonicotinoyl chloride hydrochloride (0.35 g, 1.94 mmol). The reaction mixture was stirred at room temperature overnight. The solution was concentrated under reduced pressure and added with water. The resultant precipitate was filtered and recrystallized in toluene to give N-{4-(4-(4-isopropoxypherioxy)-2,6-dimethylphenyl)thiazol-2-yl}isonicotinamide (16, 0.26 g) as light yellow solids in 79% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.80 (d, J=5.1 Hz, 2 H), 7.98 (d, J=5.7 Hz, 1 H), 7.16 (s, 1 H), 6.95 (m, 4 H), 6.69 (s, 2 H), 4.55 (t, J=6.0 Hz, 2 H), 2.05 (s, 6 H), 1.27 (s, 3 H), 1.26 (s, 3 H). ESI-MS: m/z 460.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-394585bee7324fcdae93131cc2947e8b
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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