Iodoethane → US10023592, Example 161

HRID 575649Notes

Reaction equation

HRID 575649 reaction equation
[CH2:1](I)[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH:10]1([CH2:13][O:14][C:15]2[C:16]([C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29](=[O:36])[N:28]([CH3:37])[CH:27]=3)=[N:17][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[N:19][CH:20]=2)[CH2:12][CH2:11]1>CC#N>[CH:10]1([CH2:13][O:14][C:15]2[C:16]([C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29](=[O:36])[N:28]([CH3:37])[CH:27]=3)=[N:17][C:18]([N:21]([CH2:1][CH3:2])[S:22]([CH3:25])(=[O:24])=[O:23])=[N:19][CH:20]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 118021881US10023592, Example 152

Product 1

HCID 118022401US10023592, Example 161Yield 15.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl iodide (95 mg, 0.6 mmol) and K2CO3 (55 mg, 0.4 mmol) were added to a solution of the title compound of Example 152 (80 mg, 0.2 mmol) in MeCN (5 mL). After refluxing 1 h, the mixture was cooled, concentrated under vacuum and subjected to CH2Cl2 extractive work up. HPLC purification gave the title compound (13.42 mg, yield: 15.2%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.63 (s, 1H), 8.32 (d, J=8.0 Hz, 1H), 7.90 (s, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.69 (t, J=7.6 Hz, 1H), 7.56 (t, J=7.6 Hz, 1H), 4.02 (q, J=6.8 Hz, 2H), 3.97 (d, J=7.2 Hz, 1H), 3.60 (s, 3H), 3.43 (s, 3H), 1.25 (t, J=6.8 Hz, 1H), 1.10-1.07 (m, 1H), 0.46-0.42 (m, 2H), 0.24-0.20 (m, 2H). LCMS: 429.1 (M+H)+

Workup

  1. temperatureAfter refluxing 1 h
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated under vacuum
  4. customHPLC purification

Sources & evidence

ORD record
ord-77c7bd27b81745a3ba4055bae6e29392
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

Loading…