Lithium iodide → HCID 11719751, compound

HRID 1726017Notes

Reaction equation

HRID 1726017 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 68862448HCID 68862448, compound

Product 1

HCID 11719751HCID 11719751, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 595C (205 mg, 0.4 mmol), and LiI (214 mg, 4 equiv.) in 4 mL of pyridine was reacted in a microwave at 150° C. for 35 minutes, concentrated, and 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. in 143 mg (76%) yield. MS (ESI(+)) m/e 471 (M+H)+; MS (ESI(−)) m/e 469 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ 0.99 (t, J=7.21 Hz, 6H) 1.56 (m, 6H) 2.10 (m, 2H) 2.58 (m, 4H) 2.68 (q, J=7.09 Hz, 4H) 2.90 (m, 2H) 5.71 (dt, J=11.55, 7.06 Hz, 1H) 6.79 (d, J=8.31 Hz, 1H) 6.93 (d, J=11.74 Hz, 1H) 7.12 (d, J=8.31 Hz, 1H) 7.32 (m, 2H) 7.48 (td, J=7.46, 1.22 Hz, 1H) 7.79 (dd, J=7.83, 1.22 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. custompurified 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-3beacd7b36f64a9f90dafc43d6b0b207
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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