(3-methyl-1H-indol-5-yl)methanamine → Ammonia

HRID 2228756Notes

Reaction equation

HRID 2228756 reaction equation
Cl.[CH2:2]([N:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:11][NH:12][C:13]1[C:14](=[O:24])[N:15]([CH2:20][C:21]([OH:23])=O)[C:16]([CH3:19])=[CH:17][N:18]=1)[CH:3]([CH3:5])[CH3:4].[CH3:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([CH2:35][NH2:36])[CH:33]=2)[NH:28][CH:27]=1>>[CH2:2]([N:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:11][NH:12][C:13]1[C:14](=[O:24])[N:15]([CH2:20][C:21]([NH:36][CH2:35][C:32]2[CH:33]=[C:34]3[C:29](=[CH:30][CH:31]=2)[NH:28][CH:27]=[C:26]3[CH3:25])=[O:23])[C:16]([CH3:19])=[CH:17][N:18]=1)[CH:3]([CH3:4])[CH3:5].[NH3:6]

Participants

4

Reactant 2

HCID 18470813(3-methyl-1H-indol-5-yl)methanamineHCID 699643852-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid hydrochloride

Product 2

HCID 222AmmoniaHCID 599005372-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide

Procedure

The title compound was prepared by a similar method to preparation 49 from 2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid hydrochloride [see preparation 62] and (3-methyl-1H-indol-5-yl)methylamine (72 mg, 0.45 mmol) [see preparation 36]. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (92:7:1) as the eluant, to afford the product as a foam. This was dissolved in methanol (5 ml) and hydrochloric acid (1M, 0.58 ml, 0.58 mmol), to afford the product, (56%).

Workup

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

Sources & evidence

ORD record
ord-417a65cc834d44eeb24042d7b0015cb7
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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