Isonicotinoyl chloride hydrochloride → HCID 86690851, compound

HRID 1465547Notes

Reaction equation

HRID 1465547 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F: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:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F:10])[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 86690849HCID 86690849, compound

Product 1

HCID 86690851HCID 86690851, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-chloro-6-fluoro-4-methoxyphenyl)thiazol-2-ylamine (0.10 g, 0.39 mmol) in CH2Cl2 (10 mL) was added DMAP (95 mg, 0.78 mmol) followed by isonicotinoyl chloride hydrochloride (90 mg, 0.51 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-chloro-6-fluoro-4-methoxyphenyl)thiazol-2-yl)isonicotinamide (13, 60 mg, 0.17 mmol) as white solids in 42% yield: 1H NMR (500 MHz, CDCl3) δ 8.76 (s, 2 H), 7.85 (d, J=4.5 Hz, 2 H), 7.12 (s, 1 H), 6.67 (s, 1 H), 6.45 (m, 1 H), 3.79 (s, 3H). ESI-MS: m/z 364.2 (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-cb6b03d1be30407e83c9c7962dedbbd4
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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