Methylamine → Ammonia

HRID 397631Notes

Reaction equation

HRID 397631 reaction equation
[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]2[N:21]=[C:20]([CH2:22][O:23][C:24]3[CH:41]=[CH:40][C:27]([CH2:28][N:29]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:26][CH:25]=3)[O:19][N:18]=2)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN>>[NH3:11].[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]2[N:21]=[C:20]([CH2:22][O:23][C:24]3[CH:41]=[CH:40][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=3)[O:19][N:18]=2)(=[O:9])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 570981642-[4-(3-[(2S)-1-cyclohexylmethylsulfonyl-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzyl]-1,3-isoindolinedione

Product 2

HCID 222AmmoniaHCID 572339034-[3-((2S)-1-[cyclohexylmethylsulfonyl]-2-piperidyl)-1,2,4-oxadiazol-5-ylmethoxy]benzylamine

Procedure

The title compound was prepared by a similar method to Example 11 from 2-[4-(3-[(2S)-1-cyclohexylmethylsulfonyl-2-piperidyl]-1,2,4-oxadiazol-5-ylmethoxy)benzyl]-1,3-isoindolinedione [see Preparation 23] and methylamine. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0:0 changing to 90:10:1, by volume, dichloromethane:methanol:0.88 aqueous ammonia solution to afford 4-[3-((2S)-1-[cyclohexylmethylsulfonyl]-2-piperidyl)-1,2,4-oxadiazol-5-ylmethoxy]benzylamine as a colourless oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0:0 changing to 90:10:1, by volume, dichloromethane

Sources & evidence

ORD record
ord-1cefb275f8a949d88c249560e1647183
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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