Methanol → HCID 66671605, compound

HRID 446573Notes

Reaction equation

HRID 446573 reaction equation
[C:1]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:50])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:49])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:48])[CH2:36][CH2:37][CH2:38][N:39](C(OC(C)(C)C)=O)[CH3:40])=[CH:31][CH:30]=2)[CH3:27])[CH3:19])[CH2:12][CH2:11]1.[ClH:57].O1CCOCC1.CO>O1CCOCC1>[ClH:57].[ClH:57].[ClH:57].[C:1]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:50])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([CH3:19])[C:20](=[O:49])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:48])[CH2:36][CH2:37][CH2:38][NH:39][CH3:40])=[CH:31][CH:30]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 66671667HCID 66671667, compound

Product 1

HCID 66671605HCID 66671605, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The compound (460 mg, 0.598 mmol) obtained in Example 78b was dissolved in 1,4-dioxane (6 mL), a 4 N hydrochloric acid-dioxane solution (1.49 mL, 5.98 mmol) and methanol (1 mL) were added under ice cooling, and the mixture was stirred at room temperature for 5.5 hours. After the reaction was completed, the solvent was evaporated under reduced pressure to give crude 1-(2-{methyl[6-(methyl{-4-[4-(methylamino)butanoyl]benzyl}amino)hexanoyl]amino}ethyl)piperidin-4-yl biphenyl-2-ylcarbamate trihydrochloride. The resulting crude product was used to give the title compound (101 mg; yield, 26%) as a white solid according to the method described in Example 11e.

Workup

  1. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-58fdb9d0269744b583617a75e3ed9e09
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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