Diethyl cyanophosphonate → N-[cis-1-Benzyl-6-(2-hydroxyethyl)piperidin-3-yl]-1-isopropyl-1H-indazole-3-carboxamide

HRID 602449노트

반응식

HRID 602449 반응식
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=O)=[N:5]1)([CH3:3])[CH3:2].[NH2:16][C@H:17]1[CH2:22][N:21]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:20]([CH2:30][CH2:31][OH:32])[CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O>[CH2:23]([N:21]1[C@H:20]([CH2:30][CH2:31][OH:32])[CH2:19][CH2:18][C@H:17]([NH:16][C:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=2)=[O:15])[CH2:22]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

6

반응물 4

HCID 76257Diethyl cyanophosphonateHCID 81531DiisopropylethylamineHCID 106796951-Isopropyl-1H-indazole-3-carboxylic acidHCID 672707992-[cis-5-Amino-1-benzylpiperidin-2-yl]ethanol

생성물 1

HCID 67270878N-[cis-1-Benzyl-6-(2-hydroxyethyl)piperidin-3-yl]-1-isopropyl-1H-indazole-3-carboxamide수율 57.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 1-isopropyl-1H-indazole-3-carboxylic acid (235 mg, 1.15 mmol), 2-[cis-5-amino-1-benzylpiperidin-2-yl]ethanol (322 mg, 1.37 mmol, step 8 of Example 1), N,N-diisopropylethylamine (177 mg, 1.37 mmol) in N,N-dimethylformamide (3 mL) was added diethyl cyanophosphonate (223 mg, 1.37 mmol) at room temperature. After stirring at room temperature for 20 h, the mixture was concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol/25% ammonium hydroxide (10:1:0.2) to give 276 mg (52%) of the title compound as a colorless oil.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe resulting residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol/25% ammonium hydroxide (10:1:0.2)

출처 및 근거

ORD 기록
ord-628b0bf49a864731b536be12a7e9763a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906532B2

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