Lithium iodide → HCID 68866375, compound

HRID 1725994Notes

Reaction equation

HRID 1725994 reaction equation
[CH3:1][N:2]([S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][CH2:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:19])=[O:18])[C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[C:13]([O:15]C)=[O:14].[Li+].[I-]>N1C=CC=CC=1>[CH3:1][N:2]([S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][CH2:27][CH:28]1[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]1)(=[O:18])=[O:19])[C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 68863619HCID 68863619, compound

Product 1

HCID 68866375HCID 68866375, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of Example 487A (0.064 g, 0.14 mmol) in 1.4 mL pyridine was treated with LiI (0.068 g, 0.5 mmol), heated to 150° C. for 25 minutes in a microwave reactor, and concentrated. The concentrate was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product (14.3 mg). MS (ESI(+)) m/e 458 (M+H)+; (ESI(−)) m/e 456 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.58 (dd, 1H), 7.37 (dt, 1H), 7.19 (d, 1H), 6.85 (d, 1H), 6.82 (d, 1H), 6.57 (t, 1H), 6.43 (m, 1H), 3.19 (m, 4H), 2.90 (s, 3H), 2.72, (m, 2H), 2.68 (m, 4H), 1.83 (m, 3H), 1.68 (m, 6H).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by C18 reverse-phase

Sources & evidence

ORD record
ord-759aaadfdbd041c8acfe76ffc99cfb19
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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