(1H-indol-5-yl)methanamine → 2-[3-({[(2R)-1-Cyclopentylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-(1H-indol-5-ylmethyl)acetamide

HRID 567864

Reaction equation

HRID 567864 reaction equation
Cl.[CH:2]1([N:7]2[CH2:11][CH2:10][CH2:9][C@@H:8]2[CH2:12][NH:13][C:14]2[C:15](=[O:25])[N:16]([CH2:21][C:22]([OH:24])=O)[C:17]([CH3:20])=[CH:18][N:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[NH:26]1[C:34]2[C:29](=[CH:30][C:31]([CH2:35][NH2:36])=[CH:32][CH:33]=2)[CH:28]=[CH:27]1>>[NH3:7].[CH:2]1([N:7]2[CH2:11][CH2:10][CH2:9][C@@H:8]2[CH2:12][NH:13][C:14]2[C:15](=[O:25])[N:16]([CH2:21][C:22]([NH:36][CH2:35][C:31]3[CH:30]=[C:29]4[C:34](=[CH:33][CH:32]=3)[NH:26][CH:27]=[CH:28]4)=[O:24])[C:17]([CH3:20])=[CH:18][N:19]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 54791(1H-indol-5-yl)methanamineHCID 699618882-[3-({[(2R)-1-cyclopentylpyrrolidinyl]methyl}amino)6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid hydrochloride

Product 2

HCID 222AmmoniaHCID 599005262-[3-({[(2R)-1-Cyclopentylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-(1H-indol-5-ylmethyl)acetamideYield 16%

Procedure

The title compound was prepared from 2-[3-({[(2R)-1-cyclopentylpyrrolidinyl]methyl}amino)6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid hydrochloride (preparation 145) and 1H-indol-5-ylmethylamine (preparation 8), following the procedure described in preparation 45. The crude product was purified by chromatography using a Biotage™ (KP-Sil™ 60 Å silica gel) cartridge and dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant. The product was further purified using preparative tlc and dichloromethane:methanol:0.88 ammonia (90:10:1) as eluant to afford the title compound, (11 mg, 16%).

Workup

  1. customdescribed in preparation 45
  2. customThe crude product was purified by chromatography
  3. customThe product was further purified

Sources & evidence

ORD record
ord-867200dd73ab49e59e6b532efd6603a7
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Linked notes

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