Isonicotinoyl chloride hydrochloride → HCID 86690854, compound

HRID 1465549Notes

Reaction equation

HRID 1465549 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9][CH3:10])[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]([F:8])[CH:5]=[C:4]([O:9][CH3:10])[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 86690852HCID 86690852, compound

Product 1

HCID 86690854HCID 86690854, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-chloro-4-fluoro-6-methoxyphenyl)thiazol-2-ylamine (14-2, 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-4-fluoro-6-methoxyphenyl)-thiazol-2-yl)isonicotinamide (14, 55 mg, 0.15 mmol) as white solids in 39% yield: 1H NMR (500 MHz, CDCl3) δ 8.81 (s, 2 H), 7.91 (d, J=4.7 Hz, 2 H), 7.12 (s, 1 H), 6.72 (m, 1 H), 6.50 (m, 1 H), 3.75 (s, 3 H); 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-21e643d9007344e3b853437c5c002ff8
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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