Methyl iodide → HCID 59376452, compound

HRID 1694839Notes

Reaction equation

HRID 1694839 reaction equation
[NH:1]([C:8](=[O:42])[CH:9]([C:19]1[CH:41]=[CH:40][C:22]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:24])=[CH:21][CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:43]C(C)([O-])C.[K+].CI>C1COCC1.C(OCC)(=O)C>[NH:1]([C:8](=[O:42])[C:9]([C:19]1[CH:41]=[CH:40][C:22]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:24])=[CH:21][CH:20]=1)([C:10]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:11])[CH3:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 59376442HCID 59376442, compound

Product 1

HCID 59376452HCID 59376452, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [2-({-4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)phenyl]carbamate (41 mg, 0.073 mmol) in THF (1 mL) at room temperature was added potassium tert-butoxide (85 μL, 1 M in THF, 0.085 mmol). The solution was stirred for 30 min and methyl iodide (6 μL, 0.096 mmol) was added. The reaction mixture was stirred at room temperature for 4 h, diluted with ethyl acetate, washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (20% to 65% ethyl acetate in hexanes) gave tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-1-methyl-2-oxoethyl]benzoyl}amino)phenyl]carbamate (14 mg, 33%) as a white solid: 1H NMR (600 MHz, CDCl3) δ 9.29 (s br, 1H), 8.93 (s br, 2H), 7.98 (d, J=8.2 Hz, 2H), 7.75 (d, J=7.6 Hz, 1H), 7.52-7.50 (m, 6H), 7.34 (t, J=8.2 Hz, 4H), 7.27 (d, J=7.0 Hz, 1H), 7.21 (td, J=7.9, 1.5 Hz, 1H), 7.17-7.14 (m, 3H), 6.92 (s br, 1H), 2.07 (s, 3H), 1.49 (s, 913); ESIMS calcd 579.3 (M++H), found 579.2 (M++H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 h
  2. washwashed with water (1×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel (20% to 65% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9c16b28699cf486cb5132a43af535200
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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