Triethylamine → HCID 86690813, compound

HRID 1465513Notes

Reaction equation

HRID 1465513 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[N:11]=[C:12]([NH2:15])[S:13][CH:14]=2)=[C:5]([CH3:16])[CH:4]=1.C(N(CC)CC)C.Cl.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:17][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([CH3:16])[C:6]([C:10]2[N:11]=[C:12]([NH:15][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[S:13][CH:14]=2)=[C:7]([CH3:9])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86690811HCID 86690811, compound

Product 1

HCID 86690813HCID 86690813, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(dimethylamino)-2,6-dimethylphenyl)thiazol-2-amine (1-4, 0.50 g, 2.0 mmol) in CH2Cl2 (5.1 mL) was added triethylamine (0.61 g, 6.1 mmol) followed by isonicotinoyl chloride hydrochloride (0.54 g, 3.0 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-(dimethylamino)-2,6-dimethylphenyl)thiazol-2-yl}isonicotinamide (1, 0.55 g) as yellow solids in 77% yield: 1H NMR (500 MHz, CDCl3) δ 8.64 (d, J=5.5 Hz, 2 H), 7.55 (d, J=5.5 Hz, 2 H), 6.74 (s, 1 H), 6.12 (s, 2 H), 2.89 (s, 6 H), 1.91 (s, 6 H). ESI-MS: m/z 352.6 (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-26aa8ca8a2c647acabff6a3eb152f4ec
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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