Sodium Iodide → 2-Iodo-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-6-methyl-isonicotinamide

HRID 2308537Notes

Reaction equation

HRID 2308537 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([CH3:28])[N:27]=1)[C:5]([NH:7][C:8]1[S:9][C:10]2[C:16]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[C:11]=2[N:12]=1)=[O:6].[I-:29].[Na+].I>CC(CC)=O.O1CCOCC1>[I:29][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([CH3:28])[N:27]=1)[C:5]([NH:7][C:8]1[S:9][C:10]2[C:16]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:15][CH:14]=[C:13]([O:23][CH3:24])[C:11]=2[N:12]=1)=[O:6]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 222831702-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-6-methyl-isonicotinamide

Product 1

HCID 222834182-Iodo-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-6-methyl-isonicotinamideYield 7%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 2-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-6-methyl-isonicotinamide (1.00 g, 2.39 mmol) in ethyl methyl ketone (10 ml) and dioxane (20 ml) were added sodium iodide (2.0 g, 13.3 mmol) and hydriodic acid (0.95 ml, 7.2 mmol, 57% aqueous). The mixture was then heated at 100° C. for 96 hours. The mixture was then concentrated in vacuo and the residue resuspended in dichloromethane and washed sequentially with saturated sodium bicarbonate solution, 0.1 M sodium thiosulfate solution, and saturated brine. The organic phase was then dried over Na2SO4 and the solvent evaporated. The crude product was then chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2MeOH (99:1 then 98:2), the product fractions were pooled and the solvent evaporated, to afford the title compound as a brown solid (80 mg, 7% yield), MS: m/e=511 (M+H+).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. washwashed sequentially with saturated sodium bicarbonate solution, 0.1 M sodium thiosulfate solution, and saturated brine
  3. dry with materialThe organic phase was then dried over Na2SO4
  4. customthe solvent evaporated
  5. customThe crude product was then chromatographed over SiO2 (Merck 230-400 mesh)
  6. washeluting with CH2Cl2MeOH (99:1
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-7571f43a316545fd9acffe528b13b1b4
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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