Isonicotinoyl chloride hydrochloride → HCID 91754465, compound

HRID 1484708Notes

Reaction equation

HRID 1484708 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1.Cl.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:12]1[N:13]=[C:14]([NH:17][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[S:15][CH:16]=1

Participants

5

Reactant 2

HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 118006023HCID 118006023, compound

Product 1

HCID 91754465HCID 91754465, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2,6-Dimethyl-4-nitrophenyl)thiazol-2-amine (92 mg, 0.37 mmol) in DCM (2 mL) was added DMAP (90 mg, 0.74 mmol) followed by isonicotinoyl chloride hydrochloride (85 mg, 0.48 mmol). Then the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated, and the saturated aqueous sodium bicarbonate (30 mL) was added. The aqueous solution was extracted with DCM (3×10 mL). The combined organic layers were dried with anhydrous sodium sulfate. After removal of all the solvent, the residue was purified by silica gel chromatography (hexane/EtOAc=4:1) to give INH78 (82 mg, 62%) as a white solid; mp 258-260° C. 1H NMR (400 MHz, DMSO-d6) δ 8.79-8.77 (m, 2H), 8.02 (s, 2H), 8.97-8.95 (m, 2H), 7.32 (s, 1H), 2.20 (s, 6H). 13C NMR (125 MHz, DMSO-d6) δ 164.5, 150.9, 147.2, 142.9, 139.8, 139.7, 113.4, 20.7. MS (ESI) m/z 355.0 (M+H+). HRMS calculated for C17H14N4O3SH (M+H+), 355.0865. found, 355.0867.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe saturated aqueous sodium bicarbonate (30 mL) was added
  3. extractionThe aqueous solution was extracted with DCM (3×10 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous sodium sulfate
  5. customAfter removal of all the solvent
  6. customthe residue was purified by silica gel chromatography (hexane/EtOAc=4:1)
  7. customto give INH78 (82 mg, 62%) as a white solid

Sources & evidence

ORD record
ord-13cc73f96ab2424984b63539e1eca68c
Source dataset
uspto-grants-2016_08
Patent number
US09422275B2

Reaction notes

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