Ammonium formate → HCID 44546067, 화합물

HRID 1958660노트

반응식

HRID 1958660 반응식
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:11]=2)=[CH:4][C:3]=1[N+:31]([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:11]=2)=[CH:4][C:3]=1[NH2:31]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 44545793HCID 44545793, 화합물

생성물 1

HCID 44546067HCID 44546067, 화합물수율 80%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a stirred solution of 6-(2-(4-fluoro-3-nitrobenzyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline (Example 72, prepared according to the method described in US 2008/0319012 A1) (448 mg, 1.02 mmol) in MeOH (30 mL) were added ammonium formate (257 mg, 4.08 mmol) and 10% Pd/C (30 mg) and the mixture was stirred at room temperature for 100 min. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was diluted with H2O (50 mL) and added 2N HCl solution until all remaining substances were dissolved. The aqueous solution was neutralized by addition of NH4OH solution to pH 7. The precipitate was filtered, washed with H2O, and dried under vacuum. The precipitate was purified by MPLC (MeOH:CH2Cl2=1:20 (v/v) to 1:15 (v/v)) to afford the title compound (445.5 mg, 80%). 1H NMR (300 MHz, CDCl3) δ 2.50 (3H, s), 4.10 (2H, s), 6.64-6.72 (2H, m), 6.92 (1H, d), 6.95 (1H, d), 7.24 (1H, s), 7.35-7.39 (1H, m), 7.41 (1H, dd), 7.96 (1H, dd), 8.10 (1H, d), 8.14-8.17 (2H, m), 8.91 (1H, dd). MS (ESI) m/z 410 (MH+).

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with H2O (50 mL)
  4. additionadded 2N HCl solution until all remaining substances
  5. dissolutionwere dissolved
  6. additionThe aqueous solution was neutralized by addition of NH4OH solution to pH 7
  7. filtrationThe precipitate was filtered
  8. washwashed with H2O
  9. customdried under vacuum
  10. customThe precipitate was purified by MPLC (MeOH:CH2Cl2=1:20 (v/v) to 1:15 (v/v))

출처 및 근거

ORD 기록
ord-e08ab73c801e4f8d847aa8a3a738a858
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410146B2

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