Azido(trimethyl)stannane → 2-Butyl-3-{5-[2-(1H-tetrazol-5-yl)-phenyl]-indan-1-yl}-1,3-diaza-spiro[4.4]non-1-en-4-one

HRID 1742409노트

반응식

HRID 1742409 반응식
[CH2:1]([C:5]1[N:9]([CH:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]#[N:22])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[C:8](=[O:27])[C:7]2([CH2:31][CH2:30][CH2:29][CH2:28]2)[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C(C)=CC=CC=1>[CH2:1]([C:5]1[N:9]([CH:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]4[NH:38][N:37]=[N:36][N:22]=4)=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[C:8](=[O:27])[C:7]2([CH2:28][CH2:29][CH2:30][CH2:31]2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 5104973Azido(trimethyl)stannaneHCID 190089202-[1-(2-Butyl4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-yl)-indan-5-yl]-benzonitrile

생성물 1

HCID 1784414412-Butyl-3-{5-[2-(1H-tetrazol-5-yl)-phenyl]-indan-1-yl}-1,3-diaza-spiro[4.4]non-1-en-4-one수율 31.2%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A mixture of 2-[1-(2-butyl-4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-yl)-indan -5yl]-benzonitrile (150 mg, 0.36 mmol) and trimethyltin azide (196 mg, 0.91 mmol) was heated under reflux in xylene (5.0 mL) for 25 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was chromatographed on SiO2 -gel using a gradient of 2.5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2 to give 51 mg of a colorless oil. The oil was dissolved in EtOAc and hexanes were added to precipitate the product. The white solid was filtered and dried. 1H NMR (250 MHz, d4 -MeOH): d 7.58 (m, 2 H), 7.47 (m, 2 H), 7.00 (s, 1 H), 6.85 (s, 2 H), 5.50 (t, 1 H), 2.95 (m, 2 H), 2.35 (m, 4 H), 1.90-1.41 (m), 1.22 (m, 2 H), 0.80 (t, 3 H).

후처리

  1. temperaturewas heated
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on SiO2

출처 및 근거

ORD 기록
ord-08d3cbea25c941afb3042c365a0933ec
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05338740

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