Hydrochloric Acid → 2-[3-({[(2S)-1-(Cyclopropylmethyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamide

HRID 567838Notes

Reaction equation

HRID 567838 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:18](=[O:19])[N:17]([CH2:20][C:21]([OH:23])=O)[C:16]([CH3:24])=[CH:15][N:14]=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.C1C=CC2N(O)N=NC=2C=1.Cl.CN1CCOCC1>CN(C)C=O>[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:18](=[O:19])[N:17]([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]([CH3:24])=[CH:15][N:14]=2)[CH2:3][CH2:4]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 18470813(3-methyl-1H-indol-5-yl)methanamineHCID 699625502-[5-({[(2S)-1-(cyclopropylmethyl)pyrrolidinyl]methyl}amino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetic acid hydrochloride

Product 2

HCID 222AmmoniaHCID 599005562-[3-({[(2S)-1-(Cyclopropylmethyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]-N-[(3-methyl-1H-indol-5-yl)methyl]acetamideYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[5-({[(2S)-1-(cyclopropylmethyl)pyrrolidinyl]methyl}amino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetic acid hydrochloride (preparation 76) (380 mg, 1.07 mmol), (3-methyl-1H-indol-5-yl)methylamine (preparation 36) (171 mg, 1.07 mmol), HOBT (216 mg, 1.60 mmol), WSCDI.HCl (255 mg, 1.33 mmol) and N-methylmorpholine (0.38 ml, 3.46 mmol) in N,N-dimethylformamide (4 ml), was stirred at room temperature for 24 hrs under a nitrogen atmosphere. The reaction mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (96:3.5:0.5) as eluant. This product was further purified using a Biotage™ (KP-Sil|™ 60 Å silica gel) cartridge and dichloromethane:methanol:0.88 ammonia (96:3.5:0.5) as eluant to give the title compound as a white solid, (145 mg, 29%).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe residue purified by column chromatography on silica gel
  3. customThis product was further purified

Sources & evidence

ORD record
ord-bf8bb996cfe748c694516e41babf4b70
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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