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

HRID 2228748Notes

Reaction equation

HRID 2228748 reaction equation
Cl.[CH:2]1([CH2:5][N:6]2[CH2:10][CH2:9][CH2:8][C@@H:7]2[CH2:11][NH:12][C:13]2[C:14](=[O:24])[N:15]([CH2:20][C:21]([OH:23])=O)[C:16]([CH3:19])=[CH:17][N:18]=2)[CH2:4][CH2:3]1.[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>>[NH3:6].[CH:2]1([CH2:5][N:6]2[CH2:10][CH2:9][CH2:8][C@@H:7]2[CH2:11][NH:12][C:13]2[C:14](=[O:24])[N:15]([CH2:20][C:21]([NH:36][CH2:35][C:32]3[CH:33]=[C:34]4[C:29](=[CH:30][CH:31]=3)[NH:28][CH:27]=[C:26]4[CH3:25])=[O:23])[C:16]([CH3:19])=[CH:17][N:18]=2)[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 18470813(3-methyl-1H-indol-5-yl)methanamineHCID 699621462-[3-({[(2R)-1-(cyclopropylmethyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid hydrochloride

Product 2

HCID 222AmmoniaHCID 154914822-[3-({[(2R)-1-(Cyclopropylmethyl)pyrrolidinyl]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 45 from 2-[3-({[(2R)-1-(cyclopropylmethyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid hydrochloride [see preparation 48] 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 (96:3.5:0.5) as the eluant to afford the title compound as a yellow solid, 245 mg, (55%).

Workup

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

Sources & evidence

ORD record
ord-9c3e51eb96314a65aaf0ae6b1c8d084f
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

Loading…