1-Hydroxybenzotriazole → N-methyl-5-nitro-1H-indazole-3-carboxamide

HRID 1038000

반응식

HRID 1038000 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([OH:15])=O)([O-:3])=[O:2].Cl.CN.C1C=CC2N(O)N=[N:25][C:23]=2C=1.CCN(C(C)C)C(C)C.Cl.CN(C)CCCN=C=NCC>CN1CCCC1=O.C(OCC)(=O)C>[CH3:23][NH:25][C:13]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1)=[O:15]

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 71446525-nitro-1H-indazole-3-carboxylic Acid

생성물 1

HCID 45810073N-methyl-5-nitro-1H-indazole-3-carboxamide수율 63%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a solution of compound 54 (100 mg, 0.483 mmol), methylamine hydrochloride (52.2 mg, 0.773 mmol), HOBt (130 mg, 0.966 mmol) and DIEA (0.34 mL, 1.95 mmol) in N-methylpyrrolidinone was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (148 mg, 0.773 mmol). The reaction was stirred at room temperature for 2 hrs and diluted with 10 mL of ethyl acetate. The mixture was washed with water and a yellow solid precipitated. The precipitate was collected by filtration to give compound 55 (67 mg).

후처리

  1. washThe mixture was washed with water
  2. customa yellow solid precipitated
  3. filtrationThe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-9a82de54f3a544d799cc08ca0340dcfa
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

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