Glycine, N,N-diethyl-, hydrazide → Diethyl({3-[3-(4-fluorophenyl)(1H-indazol-5-yl)](1H-1,2,4-triazol-5-yl)}methyl)amine

HRID 1353884

반응식

HRID 1353884 반응식
Cl.C(O[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[NH:6])C.C[O-].[Na+].[NH2:26][NH:27][C:28](=O)[CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32]>C(O)C.CO>[CH2:31]([N:30]([CH2:33][CH3:34])[CH2:29][C:28]1[NH:27][N:26]=[C:5]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[C:10]3[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:6]=1)[CH3:32]

참가 물질

6

반응물 3

HCID 200751Glycine, N,N-diethyl-, hydrazideHCID 10942334Sodium MethoxideHCID 22479739ethoxy[3-(4fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride

생성물 1

HCID 22480172Diethyl({3-[3-(4-fluorophenyl)(1H-indazol-5-yl)](1H-1,2,4-triazol-5-yl)}methyl)amine수율 11%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

A suspension of ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride (0.400 g, 1.25 mmol) in 4 mL of anhydrous ethanol was prepared and cooled to 0° C. An excess of a commercial solution of sodium methoxide in methanol (0.858 mL, 4.37 M)) was added followed by 3 equivalents of N-amino-2-(diethylamino)acetamide (0.545 g, 3.75 mmol) as a solid. The reaction mixture was heated to reflux temperature in a sealed tube for 2 days. The reaction was then quenched with water, the pH adjusted to neutral and the crude product extracted with ethyl acetate. The residue was purified by preparative HPLC (0.052 g, 11% yield): 1H NMR (CD3OD) δ 8.70 (s, 1H), 8.11–8.02 (m, 3H), 7.67 (d, 1H), 7.29 (td, 2H), 3.8 (s, 1H), 2.68 (q, 4H), 1.15 (t, 3H); ES-MS (m/z) 365 [M+H]+.

후처리

  1. customwas prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux temperature in a sealed tube for 2 days
  4. customThe reaction was then quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe residue was purified by preparative HPLC (0.052 g, 11% yield)

출처 및 근거

ORD 기록
ord-203c107fd87d4212b73ab8859032d631
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220771B2

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