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

HRID 841538

Reaction equation

HRID 841538 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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) δ7.45 (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).

Workup

  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

Sources & evidence

ORD record
ord-5d97ad8b85ba4525a9fced76626e05c6
Source dataset
uspto-grants-2002_04
Patent number
US06369235B1

Linked notes

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