Acetic Acid → 1-(2,6-Difluorobenzyl)-2-(2-Fluoro-4-Methoxylphenyl)-4-Aminobenzimidazole

HRID 2182091

반응식

HRID 2182091 반응식
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([N+:14]([O-])=O)[C:8]=2[N:7]=[C:6]1[C:17]1[C:22](OC)=[CH:21][CH:20]=[CH:19][C:18]=1[F:25].[C:31](O)(=[O:33])C>Cl>[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([NH2:14])[C:8]=2[N:7]=[C:6]1[C:17]1[CH:22]=[CH:21][C:20]([O:33][CH3:31])=[CH:19][C:18]=1[F:25]

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 224824531-(2,6-Difluorobenzyl)-2-(2-Fluoro-6-Methoxylphenyl)-4-Nitrobenzimidazole

생성물 1

HCID 224824601-(2,6-Difluorobenzyl)-2-(2-Fluoro-4-Methoxylphenyl)-4-Aminobenzimidazole수율 70%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

To 1-(2,6-difluorobenzyl)-2-(2-fluoro-4-methoxylphenyl)-4-nitrobenzimidazole (Example 50) (2.00 g, 4.98 mmol) dissolved in acetic acid (20 mL) was added SnCl2x2H2O (9.02 g) dissolved in concentrated HCl (8 mL). After stirring for 30 min at room temperature, the mixture was concentrated. The residue was diluted with CH2Cl2 and washed with NaHCO3 (sat. aq.) and NaCl (sat. aq.). The combined washings were dried (Na2SO4), filtered, and evaporated. The crude product was recrystallized from methanol to give 3.26 g of white crystals, (8.78 mmol, 70% yield). M.p. 200-202° C. 1H-NMR (200 MHz, CD2Cl2) δ 7.45 (m, 1H, H4′), 7.22 (m, 1H, H4″), 7.05 (dd, J=7.8, 7.6 Hz, 1H, H6), 6.85-6.72 (m, 5H, H3″,5″), 6.50 (dd, J=7.7, 1.0 Hz, 1H, H5), 5.21 (d, J=5.4 Hz, 2H, CH2PhF2 (rotamers)), 4.34 (br, 2H, NH2), 3.72 (s, 3H, OCH3).

후처리

  1. additionwas added SnCl2x2H2O (9.02 g)
  2. concentrationthe mixture was concentrated
  3. additionThe residue was diluted with CH2Cl2
  4. washwashed with NaHCO3 (sat. aq.) and NaCl (sat. aq.)
  5. dry with materialThe combined washings were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was recrystallized from methanol

출처 및 근거

ORD 기록
ord-53052f8c01954de490669692cf69a00a
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894068B2

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