Isonicotinoyl chloride hydrochloride → HCID 86690841, compound

HRID 1465539Notes

Reaction equation

HRID 1465539 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[C:11]1[N:12]=[C:13]([NH2:16])[S:14][CH:15]=1.Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[C:11]1[N:12]=[C:13]([NH:16][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[S:14][CH:15]=1

Participants

5

Reactant 2

HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86690839HCID 86690839, compound

Product 1

HCID 86690841HCID 86690841, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2,6-dichloro-4-methoxyphenyl)thiazol-2-ylamine (10-5, 0.10 g, 0.36 mmol) in CH2Cl2 (10 mL) was added DMAP (88 mg, 0.72 mmol) followed by isonicotinoyl chloride hydrochloride (83 mg, 0.47 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 collected and recrystallized in toluene to give N-(4-(2,6-dichloro-4-methoxyphenyl)thiazol-2-yl)isonicotinamide (50 mg, 0.13 mmol) as white solids in 37% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.80 (d, J=5.8 Hz, 2 H), 7.99 (d, J=6.0 Hz, 2 H), 7.31 (d, J=1.7 Hz, 1 H), 7.26 (s, 1 H), 7.22 (d, J=1.7 Hz, 1 H), 3.75 (s, 3 H). ESI-MS: m/z 381.4 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-3ffe0a4cc3f947c8ab1464f6d12309b8
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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