Lithium iodide → HCID 11633910, compound

HRID 1726005Notes

Reaction equation

HRID 1726005 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[CH2:4][CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[C:19]=1[C:28]([O:30]C)=[O:29])(=[O:16])=[O:15])[CH3:2].[Li+].[I-]>N1C=CC=CC=1>[CH2:32]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH:17][C:18]1[CH:27]=[CH:26][C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[C:19]=1[C:28]([OH:30])=[O:29])(=[O:16])=[O:15])[CH3:33]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 11518441HCID 11518441, compound

Product 1

HCID 11633910HCID 11633910, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of Example 529D (373 mg, 0.8 mmol) and LiI (428 mg, 4 equiv.) in 8 mL of pyridine was heated at 150° C. for 35 minutes in a microwave. The product was purified in two fractions by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 0% to 95% acetonitrile/0.1% aqueous TFA over 12 minutes (15 minute run time) at a flow rate of 70 mL/min to yield 257 mg (70%) of the desired product. MS (ESI(+)) m/e 457 (M+H)+; MS (ESI(−)) m/e 455 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ 1.20 (t, J=7.27 Hz, 6H) 1.64 (m, 4H) 2.61 (m, 6H) 3.18 (m, 6H) 6.21 (ddd, J=15.40, 6.90, 6.79 Hz, 1H) 6.65 (m, 1H) 6.92 (d, J=8.23 Hz, 1H) 7.25 (d, J=15.64 Hz, 1H) 7.37 (t, J=8.23 Hz, 1H) 7.58 (t, J=7.96 Hz, 1H) 7.67 (m, 1H) 7.75 (dd, J=7.96, 1.37 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-1da774f596b44e66a21835d1eca30af0
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…