HCID 42639924, compound → HCID 42640083, compound

HRID 660027Notes

Reaction equation

HRID 660027 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]2[NH:6][C:7]([C:9]3[C:10]([CH3:28])=[C:11]4[C:15](=[CH:16][CH:17]=3)[N:14]([CH2:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[CH2:13][CH2:12]4)=[N:8][C:4]=2[C:3]=1[CH3:31]>C1(C)C=CC=CC=1.O=[Mn]=O>[F:1][C:2]1[CH:30]=[CH:29][C:5]2[NH:6][C:7]([C:9]3[C:10]([CH3:28])=[C:11]4[C:15](=[CH:16][CH:17]=3)[N:14]([CH2:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[CH:13]=[CH:12]4)=[N:8][C:4]=2[C:3]=1[CH3:31]

Participants

4

Reactant 1

HCID 42639924HCID 42639924, compound

Product 1

HCID 42640083HCID 42640083, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 5-fluoro-4-methyl-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole (40 mg, 0.10 mmol) in toluene (2 mL) was added MnO2 (44 mg, 0.51 mmol). After 1 h at 70° C., the mixture was cooled, filtered through diatamaceous earth, and concetrated. The crude residue was purified by FCC to give the title compound (35 mg, 84%). MS: mass calcd. for C26H31FN4, 418.25; m/z found, 421.3 [M+H]+. 1H NMR (CD3OD): 7.42-7.33 (m, 3H), 7.30 (d, J=3.2, 1H), 6.99 (dd, J=10.4, 8.7, 1H), 6.62 (d, J=2.7, 1H), 4.22 (t, J=6.9, 6.9, 2H), 2.86-2.78 (m, 2H), 2.65 (s, 3H), 2.50 (d, J=1.2, 3H), 2.22 (s, 3H), 2.00-1.83 (m, 4H), 1.73-1.56 (m, 2H), 1.31-1.11 (m, 5H).

Workup

  1. temperaturethe mixture was cooled
  2. filtrationfiltered through diatamaceous earth
  3. customThe crude residue was purified by FCC

Sources & evidence

ORD record
ord-141e23856fd542c3a120dc385dcffe02
Source dataset
uspto-grants-2011_12
Patent number
US08084466B2

Reaction notes

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