Hydrochloride methanol → 1-[2-(Methyl{6-[(4-methyl-5-{methyl[2-(methylamino)ethyl]carbamoyl}thiophen-2-yl)amino]hexanoyl}amino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate

HRID 446587Notes

Reaction equation

HRID 446587 reaction equation
[C:1]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:49])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:48])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[S:28][C:29]([C:33](=[O:47])[N:34]([CH2:36][CH2:37][N:38](C(OC(C)(C)C)=O)[CH3:39])[CH3:35])=[C:30]([CH3:32])[CH:31]=2)[CH3:19])[CH2:12][CH2:11]1.Cl.CO>C1(C)C=CC=CC=1>[C:1]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:49])[O:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][N:18]([CH3:19])[C:20](=[O:48])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[S:28][C:29]([C:33](=[O:47])[N:34]([CH3:35])[CH2:36][CH2:37][NH:38][CH3:39])=[C:30]([CH3:32])[CH:31]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 666713931-(2-{[6-({5-[{2-([tert-Butoxycarbonyl)(methyl)amino]ethyl}(methyl)carbamoyl]-4-methylthiophen-2-yl}amino)hexanoyl](methyl)amino}ethyl)piperidin-4-yl biphenyl-2-ylcarbamate

Product 1

HCID 666717001-[2-(Methyl{6-[(4-methyl-5-{methyl[2-(methylamino)ethyl]carbamoyl}thiophen-2-yl)amino]hexanoyl}amino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamateYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound (153 mg, 0.201 mmol) obtained in Example 89d was dissolved in 2 N hydrochloric acid-methanol (2.01 mL, 4.01 mmol), and the mixture was stirred at room temperature for 2 hours. Toluene was added to the reaction mixture, the solvent was evaporated under reduced pressure, the resulting residue was dissolved in ethyl acetate, and the mixture was adjusted to pH 10 with a 1 N aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate (×2) and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=100:0→methylene chloride:methanol=10:1, v/v) to give the title compound (122 mg; yield, 92%) as a white solid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in ethyl acetate
  3. extractionThe mixture was extracted with ethyl acetate (×2)
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-9de4578dc2d14fceb9cb2971cc005b17
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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