Hydrochloric Acid → N-(1H-Indol-5-ylmethyl)-2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetamide

HRID 567861

Reaction equation

HRID 567861 reaction equation
C1C=CC2N(O)N=[N:7]C=2C=1.Cl.CN1CCOCC1.[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][NH2:29])=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.[CH2:30]([N:34]1[CH2:38][CH2:37][CH2:36][C@@H:35]1[CH2:39][NH:40][C:41]1[C:42](=[O:52])[N:43]([CH2:48][C:49](O)=[O:50])[C:44]([CH3:47])=[CH:45][N:46]=1)[CH:31]([CH3:33])[CH3:32]>CN(C)C=O>[NH3:7].[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][NH:29][C:49](=[O:50])[CH2:48][N:43]3[C:44]([CH3:47])=[CH:45][N:46]=[C:41]([NH:40][CH2:39][C@H:35]4[CH2:36][CH2:37][CH2:38][N:34]4[CH2:30][CH:31]([CH3:32])[CH3:33])[C:42]3=[O:52])=[CH:25][CH:26]=2)[CH:21]=[CH:20]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 54791(1H-indol-5-yl)methanamineHCID 757711-HydroxybenzotriazoleHCID 599005362-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid

Product 2

HCID 222AmmoniaHCID 59900500N-(1H-Indol-5-ylmethyl)-2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetamideYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HOBT (24 mg, 0.18 mmol), WSCDI.HCl (29 mg, 0.15 mmol), N-methylmorpholine (39 ml, 0.36 mmol) and 1H-indol-5-ylmethylamine (preparation 8) (19 mg, 0.13 mmol) were added to a solution of 2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid (preparation 62) (38 mg, 0.12 mmol) in N,N-dimethylformamide (2 ml), and the reaction was stirred at room temperature overnight. The mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant. The product was re-purified using a Biotage™ (KP-Sil™ 60 Å silica gel) cartridge and dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant to afford the title compound, (16 mg, 30%).

Workup

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

Sources & evidence

ORD record
ord-98d86336f98e44278b4f3cb030403ab0
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Linked notes

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