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 1712955노트

반응식

HRID 1712955 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e0910065db3e4e828f91aa01a2df9974
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795249B2

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