Triethylamine → 5-isopropyl-1-methyl-1H-indazole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide

HRID 25276노트

반응식

HRID 25276 반응식
[CH:1]([C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH3:13])[N:8]=[CH:7][C:6]=2[C:5]=1[C:14](Cl)=[O:15])([CH3:3])[CH3:2].[C:17]1(C)[CH:22]=[CH:21][C:20]([NH:23][CH:24]2[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25]2)=[CH:19][CH:18]=1.[CH2:34](N(CC)CC)[CH3:35]>C1COCC1.C(OCC)(=O)C>[CH2:32]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH:24]1[N:23]([CH2:20][C:19]1[CH:18]=[CH:17][C:22]([CH3:21])=[CH:35][CH:34]=1)[C:14]([C:5]1[C:6]2[CH:7]=[N:8][N:9]([CH3:13])[C:10]=2[CH:11]=[CH:12][C:4]=1[CH:1]([CH3:3])[CH3:2])=[O:15]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 15637824HCID 15637824, 화합물HCID 225669405-Isopropyl-1-methyl-1H-indazole-4-carbonyl chloride

생성물 1

HCID 207604485-isopropyl-1-methyl-1H-indazole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

5-Isopropyl-1-methyl-1H-indazole-4-carbonyl chloride (0.618 mmol, 1.0 eq) (30) in 5 ml of THF is added to a solution of (4-tolyl)-indan-2-yl-amine (147 mg, 0.618 mmol) (31) in 5 ml of tetrahydrofuran containing 250 mg of triethylamine at 0° C. The resulting mixture is stirred at room temperature overnight, diluted with 20 ml of ethyl acetate, washed with water and brine, and dried over sodium sulfate. Concentration and purification by silica gel chromatography affords 168 mg of 5-isopropyl-1-methyl-1H-indazole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide (32). 1H NMR (400 MHz, CDCl3) 7.89 (1H, s), 7.42˜6.92 (10H, m), 4.95 (1H, d, J=15.2 Hz), 4.66 (1H, d, J=15.2 Hz), 4.551 (1H, m), 4.05 (3H, s), 3.26˜2.73 (5H, m), 2.36 (3H, s), 1.34 (6H, dd, J=1.6, 6.8Hz). MS (+VE) m/z 438 (M++1).

후처리

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration and purification by silica gel chromatography

출처 및 근거

ORD 기록
ord-1c2e53d2e6464627981d6eff1862f342
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858637B2

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