1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-{3-Pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)carbonyl]-4,5-dihydro-1h-pyrazol-5-yl}phenol

HRID 1712955ノート

反応式

HRID 1712955 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[NH:9][N:8]=2)[CH:2]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[S:29][C:28]([C:30](O)=[O:31])=[CH:27][CH:26]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[N:9]([C:30]([C:28]3[S:29][C:25]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=4)=[CH:26][CH:27]=3)=[O:31])[N:8]=2)[CH:2]=1

参加物

5

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 7364825-(Pyridin-2-yl)thiophene-2-carboxylic acidHCID 226963962-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol

生成物 1

HCID 249635882-{3-Pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)carbonyl]-4,5-dihydro-1h-pyrazol-5-yl}phenol収率 72%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (1.01 g, 4.22 mmol) and 5-pyridin-2-ylthiophene-2-carboxylic acid (0.886 g, 4.32 mmol) in DCM (50 mL) was added EDCI (0.970 g, 5.10 mmol). The reaction mixture was allowed to stir at rt overnight. The solution was filtered and the resulting precipitate was washed with DCM to give a light tan solid. The filtrate was concentrated and the resulting residue was purified by column chromatography to give a yellow solid. The two batches of product were combined to give 2-{3-pyridin-3-yl-1-[(5-pyridin-2-yl-2-thienyl)carbonyl]4,5-dihydro-1H-pyrazol-5-yl}phenol (I-76) (1.293 g, 72%) as a tan solid. 1H NMR (400 MHz, d6-DMSO, HCl salt) δ: 9.71-9.84 (bs, 1H), 9.11-9.16 (m, 1H), 8.72-8.77 (m, 1H), 8.60-8.65 (m, 1H), 8.35-8.42 (m, 1H), 8.06 (d, 1H), 8.01-8.04 (m, 1H), 7.84-7.94 (m, 2H), 7.66-7.73 (m, 1H), 7.34-7.41 (m, 1H), 7.04-7.12 (m, 1H), 6.93-6.99 (m, 1H), 6.82-6.87 (m, 1H), 6.73 (t, 1H), 5.87 (dd, 1H), 3.92 (dd, 1H), and 3.22 (dd, 1H). LCMS: (FA) ES+ 427.5, ES-425.4.

後処理

  1. filtrationThe solution was filtered
  2. washthe resulting precipitate was washed with DCM
  3. customto give a light tan solid
  4. concentrationThe filtrate was concentrated
  5. customthe resulting residue was purified by column chromatography
  6. customto give a yellow solid

出典と根拠

ORDレコード
ord-e0910065db3e4e828f91aa01a2df9974
出典データセット
uspto-grants-2010_09
特許番号
US07795249B2

反応ノート

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