Sodium Iodide → HCID 20745821, compound

HRID 2308005Notes

Reaction equation

HRID 2308005 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[C:9]([NH:10][CH:11]([CH2:14]OS(C)(=O)=O)[CH2:12][CH3:13])=[CH:8][C:7]([CH3:20])=[N:6][C:5]=1[O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=1[CH3:30].[I-].[Na+].[CH2:34]([NH2:36])[CH3:35].C(N(CC)CC)C>C(#N)C>[CH3:1][O:2][C:3](=[O:31])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][NH:36][CH2:34][CH3:35])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:20])=[N:6][C:5]=1[O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=1[CH3:30]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6341EthylamineHCID 8471TriethylamineHCID 86584330HCID 86584330, compound

Product 1

HCID 20745821HCID 20745821, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-(4-chloro-2,6-dimethyl-phenoxy)-4-(1-methanesulfonyloxymethyl-propylamino)-6-methyl-nicotinic acid methyl ester in acetonitrile was treated with sodium iodide, ethylamine and triethylamine. The resulting mixture was heated to 70° C. overnight, then 85° C. for 6 hrs, then 100° C. overnight until tic showed no starting material. The resulting mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried, concentrated, and purified to give the title compound as an oil. 1H NMR(CDCl3) d 8.06(d, 1H), 7.02(s, 2H), 6.31(s, 1H), 3.88(s, 3H), 3.86(m,1H), 2.85(m, 4H), 2.12(s,3H), 2.07(s, 6H), 1.64(m, 1H), 1.60(m, 1H), 1.27(m, 3H), .99(t, 3H)

Workup

  1. custom100° C. overnight
  2. customThe resulting mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-9f30d151bece406aa93cb72da48fd7e1
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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