HCID 86616471, compound → HCID 57973889, compound

HRID 1864805Notes

Reaction equation

HRID 1864805 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]1[C:10]([N+]([O-])=O)=[CH:9][N:8]=[C:7]([C:14]2[CH:15]=[CH:16][C:17]([F:38])=[C:18]([CH:37]=2)[CH2:19][N:20]([CH2:30][CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:6]=1.[H][H]>C(OCC)(=O)C.[Pd]>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([N:20]([CH2:19][C:18]2[CH:37]=[C:14]([C:7]3[CH:6]=[C:5]4[CH:4]=[CH:3][NH:2][C:10]4=[CH:9][N:8]=3)[CH:15]=[CH:16][C:17]=2[F:38])[CH2:30][CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:29])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 86616471HCID 86616471, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57973889HCID 57973889, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-{5-[4-((E)-2-Dimethylamino-vinyl)-5-nitro-pyridin-2-yl]-2-fluoro-benzyl}-4-fluoro-N-(2-pyrrolidin-1-yl-ethyl)-benzamide (485 mg, 0.9 mmol) in 30 mL of ethyl acetate was treated with 100 mg of 10% Pd/C under 3 bar of hydrogen for 18 h. The mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was chromatographed (alumina, elution with 2% methanol/dichloromethane) to afford 230 mg of product. LC/MS: Retention time, 1.79 min; (M+H)=461. 1H NMR (400 MHz, DMSO-D6) δ ppm: 1.61 (br s, 4H) 2.37 (br ss, 2H) 2.56-2.71 (br s, 2H) 3.45 (t, J=6.26 Hz, 2H) 4.75 (s, 2H) 6.55 (s, 1H) 7.17-7.28 (m, 3H) 7.45-7.52 (m, 2H) 7.56 (t, J=2.64 Hz, 1H) 8.00 (ddd, J=8.30, 5.44, 2.31 Hz, 2H) 8.07 (d, J=7.47 Hz, 1H) 8.82 (s, 1H) 11.40 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed
  4. wash(alumina, elution with 2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-5f6d78878fc84c2f9726e7cbc9d3cb3a
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

Loading…