Lithium iodide → HCID 11561873, compound

HRID 1726020Notes

Reaction equation

HRID 1726020 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[C:20]=1[C:29]([O:31]C)=[O:30])(=[O:17])=[O:16])[CH3:2].[Li+].[I-]>N1C=CC=CC=1>[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[C:20]=1[C:29]([OH:31])=[O:30])(=[O:17])=[O:16])[CH3:34]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 68863786HCID 68863786, compound

Product 1

HCID 11561873HCID 11561873, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 597A (310 mg, 0.6 mmol), and LiI (322 mg, 4 equiv.) in 6 mL of pyridine was reacted in two vials in a microwave at 150° C. for 35 minutes and concentrated. The concentrate was purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 95% acetonitrile/10 mM aqueous ammonium acetate over 12 minutes (15 minute run time) at a flow rate of 70 mL/min. The product was combined with a sample of Example 596B to provide 256 mg of a 5:4 mixture of Example 596B and Example 597B.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)
  3. customover 12 minutes
  4. custom(15 minute run time)

Sources & evidence

ORD record
ord-17f2b460c7674bc9825c2b054b252c16
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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