Lithium iodide → HCID 11561873, compound

HRID 1726018Notes

Reaction equation

HRID 1726018 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[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]([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 68864649HCID 68864649, compound

Product 1

HCID 11561873HCID 11561873, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 596A (420 mg, 0.9 mmol), and LiI (482 mg, 4 equiv.) in 9 mL of pyridine was reacted in two vials in a microwave at 150° C. for 35 minutes. After concentration, the crude product 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 NH4OAc over 12 minutes (15 minute run time) at a flow rate of 70 mL/min. in 36 mg (8%) yield. MS (ESI(+)) m/e 471 (M+H)+; MS (ESI(−)) m/e 469 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ 1.21 (t, J=6.72 Hz, 6H) 1.55 (m, 4H) 2.01 (s, 2H) 2.28 (q, J=6.11 Hz, 2H) 2.55 (s, 2H) 2.86 (s, 2H) 3.05 (m, 6H) 6.30 (m, 1H) 6.81 (m, 1H) 7.11 (d, J=8.31 Hz, 1H) 7.17 (d, J=15.89 Hz, 1H) 7.35 (m, 1H) 7.51 (t, J=6.97 Hz, 1H) 7.57 (m, 1H) 7.93 (m, 1H).

Workup

  1. concentrationAfter concentration
  2. customthe crude product 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)
  5. customyield

Sources & evidence

ORD record
ord-d6137cf2090147d787ef8e7f92697c6b
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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