2-[3-Chloro-5-({[(2R)-1-(cyclopropylmethyl)piperidinyl]methyl}amino)-2-methyl-6-oxo-1(6H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide → Ammonia

HRID 567836Notes

Reaction equation

HRID 567836 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]2[CH2:16][CH:17]2[CH2:19][CH2:18]2)[C:5](=[O:20])[N:4]([CH2:21][C:22]([NH:24][CH2:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[C:29]3[CH3:35])=[O:23])[C:3]=1[CH3:36]>[OH-].[Pd+2].[OH-]>[CH:17]1([CH2:16][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C@@H:10]2[CH2:9][NH:8][C:6]2[C:5](=[O:20])[N:4]([CH2:21][C:22]([NH:24][CH2:25][C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[NH:31][CH:30]=[C:29]4[CH3:35])=[O:23])[C:3]([CH3:36])=[CH:2][N:7]=2)[CH2:19][CH2:18]1.[NH3:4]

Participants

4

Reactant 1

HCID 699613972-[3-Chloro-5-({[(2R)-1-(cyclopropylmethyl)piperidinyl]methyl}amino)-2-methyl-6-oxo-1(6H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide

Product 2

HCID 222AmmoniaHCID 154914862-[3-({[(2R)-1-(cyclopropylmethyl)piperidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

The title compound was prepared by a similar method to preparation 44 from 2-[3-chloro-5-({[(2R)-1-(cyclopropylmethyl)piperidinyl]methyl}amino)-2-methyl-6-oxo-1(6H) pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide [see preparation 73] and palladium hydroxide. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:1) as the eluant to afford the product as a white solid, (36%).

Workup

  1. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-84cc93c5d11d472d94a2fa38cba7737c
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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