p-Toluenesulfonic acid monohydrate → N-hydroxy-N'-methyl-2-[methyl({4'-[3-(morpholin-4-yl)propoxy]biphenyl-4-yl}carbonyl)amino]propanediamide 4-methylbenzenesulfonate

HRID 1519675Notes

Reaction equation

HRID 1519675 reaction equation
[OH:1][NH:2][C:3](=[O:35])[CH:4]([N:9]([CH3:34])[C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:11])[C:5]([NH:7][CH3:8])=[O:6].[CH3:36][C:37]1[CH:38]=[CH:39][C:40]([S:43]([OH:46])(=[O:45])=[O:44])=[CH:41][CH:42]=1.O>C1COCC1>[CH3:36][C:37]1[CH:38]=[CH:39][C:40]([S:43]([OH:46])(=[O:45])=[O:44])=[CH:41][CH:42]=1.[OH:1][NH:2][C:3](=[O:35])[CH:4]([N:9]([CH3:34])[C:10]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)=[O:11])[C:5]([NH:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86679255N-hydroxy-N'-methyl-2-[methyl({4'-[3-(morpholin-4-yl)propoxy]biphenyl-4-yl}carbonyl)amino]propanediamide2×

Product 1

HCID 86679256N-hydroxy-N'-methyl-2-[methyl({4'-[3-(morpholin-4-yl)propoxy]biphenyl-4-yl}carbonyl)amino]propanediamide 4-methylbenzenesulfonateYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF (1.0 mL) suspension of N-hydroxy-N′-methyl-2-[methyl({4′-[3-(morpholin-4-yl)propoxy]biphenyl-4-yl}carbonyl)amino]propanediamide (Compound 7, 24 mg) as obtained in Example 4-(5), p-TsOH.H2O (9.5 mg) was added, and the mixture was stirred for 10 minutes at room temperature. The precipitate was collected by filtration to obtain N-hydroxy-N′-methyl-2-[methyl({4′-[3-(morpholin-4-yl)propoxy]biphenyl-4-yl}carbonyl)amino]propanediamide 4-methylbenzenesulfonate (Compound 7b, white solid) (26 mg, 79%).

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-6026e1eaffdf42f3a463b598d1ea8dff
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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