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

HRID 25276ノート

反応式

HRID 25276 の反応式
[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]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 15637824HCID 15637824、化合物HCID 225669405-Isopropyl-1-methyl-1H-indazole-4-carbonyl chloride

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1c2e53d2e6464627981d6eff1862f342
出典データセット
uspto-grants-2005_02
特許番号
US06858637B2

反応ノート

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