Triethylamine → HCID 86690817, compound

HRID 1465517Notes

Reaction equation

HRID 1465517 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:10][C:9]=1[CH3:24].C(N(CC)CC)C.Cl.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([NH:7][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[N:4][C:3]=1[C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:10][C:9]=1[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86690815HCID 86690815, compound

Product 1

HCID 86690817HCID 86690817, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-amine (2-4, 325 mg, 0.70 mmol) in CH2Cl2 (10 ml) was added triethylamine (0.50 mL, 1.7 mmol) followed by isonicotinoyl chloride hydrochloride (302.5 mg, 3.4 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-{5-bromo-4-(4-(4-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-yl}isonicotinamide (2, 345 mg) as white solids in 99% yield: 1H NMR (500 MHz, DMSO-d6) δ 13.3 (s, 1 H), 8.82 (m, 2 H), 7.98 (m, 2 H), 7.05 (d, J=9.0 Hz, 2 H), 6.99 (d, J=9.0 Hz, 2 H), 6.70 (s, 2 H), 3.76 (s, 3 H), 1.99 (s, 6 H); ESI-MS: m/z 509.6, 511.1 (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-b0297628928c42fa8c32bf6348852f56
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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