Triethylamine → HCID 86690870, compound

HRID 1465567Notes

Reaction equation

HRID 1465567 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:27]=[CH:26][C:10]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([C:19]3[N:20]=[C:21]([NH2:24])[S:22][CH:23]=3)=[C:14]([CH3:25])[CH:13]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:27]=[CH:26][C:10]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([C:19]3[N:20]=[C:21]([NH:24][C:36](=[O:43])[C:37]4[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=4)[S:22][CH:23]=3)=[C:14]([CH3:25])[CH:13]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86690868HCID 86690868, compound

Product 1

HCID 86690870HCID 86690870, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-(4-(3-methoxypropoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-amine (21-5, 0.28 g, 0.74 mmol) in CH2Cl2 (5.0 mL) was added triethylamine (0.5 mL, 3.59 mmol) followed by isonicotinoyl chloride hydrochloride (0.22 g, 1.22 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-(3-methoxypropoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide (21, 0.99 mg) as light yellow solids in 27% yield: 1H NMR (500 MHz, DMSO-d6) δ 13.00 (s, 1 H), 8.81 (s, 2 H), 7.99 (d, J=5.7 Hz, 2 H), 7.15 (s, 1 H), 6.98 (m, 4 H), 6.68 (s, 2 H), 4.00 (t, J=6.3 Hz, 2 H), 3.47 (t, J=6.3 Hz, 1 H), 2.05 (s, 6 H), 1.94 (t, J=6.3 Hz, 2 H). ESI-MS: m/z 489.7 (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-fc4288818114476d8300ac8aea0e80e9
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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