Triethylamine → HCID 86690848, compound

HRID 1465545Notes

Reaction equation

HRID 1465545 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:26]=[CH:25][C:9]([O:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([C:18]3[N:19]=[C:20]([NH2:23])[S:21][CH:22]=3)=[C:13]([CH3:24])[CH:12]=2)=[CH:8][CH:7]=1.C(N(CC)CC)C.Cl.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([C:18]3[N:19]=[C:20]([NH:23][C:35](=[O:42])[C:36]4[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=4)[S:21][CH:22]=3)=[C:13]([CH3:24])[CH:12]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86690846HCID 86690846, compound

Product 1

HCID 86690848HCID 86690848, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-(4-(2-methoxyethoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-amine (12-6, 322.3 mg, 0.90 mmol) in CH2Cl2 (10.0 ml) was added triethylamine (0.40 mL, 2.6 mmol) followed by isonicotinoyl chloride hydrochloride (387.2 mg, 2.1 mmol). The reaction mixture was stirred at room temperature overnight. The solution was concentrated under reduced pressure and added with hot water. The resultant precipitate was filtered and dried under vacuum to give N-(4-{4-(4-(2-methoxyethoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide (12, 230 mg) as white solids in 56% yield: 1H NMR (500 MHz, DMSO-d6) δ 13.0 (brs, 1 H), 8.78 (d, J=5.8 Hz, 2 H), 7.98 (d, J=5.8 Hz, 2 H), 7.12 (s, 1 H), 6.96-7.00 (m, 4 H), 6.67 (s, 2 H), 4.01-4.07 (m, 2 H), 3.63-3.64 (m, 2 H), 3.26 (s, 3 H), 2.03 (s, 6 H). ESI-MS: m/z 476.4 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-4510608f219648479db3ec7e2429e3e2
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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