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

HRID 567861

반응식

HRID 567861 반응식
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

참가 물질

8

반응물 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

생성물 2

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-98d86336f98e44278b4f3cb030403ab0
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180627B2

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