HCID 69417337, compound → HCID 69420062, compound

HRID 1373201Notes

Reaction equation

HRID 1373201 reaction equation
[CH3:1][O:2][C:3]([C:5]1([F:25])[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[CH2:23])=[CH:18][C:17]=2[F:24])=[CH:13][C:8]2=[N:9][CH2:10][N:11]([CH3:12])[C:7]2=[CH:6]1)=[O:4]>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1([F:25])[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:17]=2[F:24])=[CH:13][C:8]2=[N:9][CH2:10][N:11]([CH3:12])[C:7]2=[CH:6]1)=[O:4]

Participants

4

Reactant 1

HCID 69417337HCID 69417337, compound

Product 1

HCID 69420062HCID 69420062, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-Fluoro-6-(2-fluoro-4-vinyl-phenylamino)-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester (1.5 g, 4.35 mmol) was combined with 10% palladium/carbon (0.4 g) in tetrahydrofuran (50 mL). The resultant solution was hydrogenated at 4295 psi for 56 min. The reaction mixture was filtered and concentrated in vacuo to afford 0.91 g. Recrystallization from dichlormethane-hexane afforded pure 6-(4-Ethyl-2-fluoro-phenylamino)-5-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester, m.p. 238° C.; 1H NMR (400 MHz, CD3OD) δ 8.28 (s, 1 H), 8.24 (br s, 1 H), 8.10 (s, 1 H), 6.93 (dd, J=12.4, 1.5 Hz, 1 H), 6.80 (brd, J=8.3 Hz, 1 H), 6.61 (td, J=8.6,5.4 Hx, 1 H), 3.94 (s,3 H), 3.92 (s, 3 H), 2.55 (q, J=5.6 Hz, 2 H), 1.20 (t, J=5.6 Hz, 3 H). Anal. Calcd/Found for C18H15F2N3O2: C, 62.60/62.11; H, 4.96/4.80; N, 12.15, 11.80.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto afford 0.91 g
  4. customRecrystallization from dichlormethane-hexane afforded pure 6-(4-Ethyl-2-fluoro-phenylamino)-5-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester, m.p. 238° C.

Sources & evidence

ORD record
ord-b972718aca0646bfb38722e6e59ac3b4
Source dataset
uspto-grants-2007_01
Patent number
US07160915B2

Reaction notes

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