Pyridine → HCID 178480360, compound

HRID 1670648Notes

Reaction equation

HRID 1670648 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:36]=1)[O:7][CH2:8][C:9]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH:21]2[OH:27])=[C:15]([N+:28]([O-])=O)[CH:14]=1.C(N(CC)CC)C.N1C=CC=CC=1.C1C=CC(O[C:57](OC2C=CC=CC=2)=[N:58][C:59]#[N:60])=CC=1>O1CCCC1.[Pt]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:36]=1)[O:7][CH2:8][C:9]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]2[N:19]([C@H:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][C@@H:21]3[OH:27])/[C:57](=[N:58]/[C:59]#[N:60])/[NH:28][C:15]=2[CH:14]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 67336037HCID 67336037, compound

Product 1

HCID 178480360HCID 178480360, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 4-[4-((E)-3,7-difluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-2-nitro-phenylamino]-1-methyl-piperidin-3-ol (0.012 mol, 5.97 g) in tetrahydrofuran (50 mL). Add triethylamine (0.024 mol, 2.44 g) and 10% platinum on carbon (2.9 g) and hydrogenate in a Parr shaker at 50 psi (H2) at room temperature for 4 h. Filter off the catalyst through diatomaceous earth. Add pyridine (50 mL) and diphenyl N-cyanocarbonimidate (0.012 mol, 2.88 g) to the filtrate. Stir at room temperature for 16 h and then heat at 60-70° C. for 8 h. Remove the solvent under reduced pressure, dissolve the residue in dichloromethane and wash with water and saturated sodium bicarbonate solution. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue on a silica gel column using 5% methanol in dichloromethane as eluent to obtain the title compound (1.7 g, 27%) as an off-white solid. LC-MS m/z 514.4 [M+H]+.

Workup

  1. filtrationFilter off the catalyst through diatomaceous earth
  2. temperatureheat at 60-70° C. for 8 h
  3. customRemove the solvent under reduced pressure
  4. dissolutiondissolve the residue in dichloromethane
  5. washwash with water and saturated sodium bicarbonate solution
  6. dry with materialDry the organic layer over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customPurify the residue on a silica gel column

Sources & evidence

ORD record
ord-b08580387cc74fd3a45a51cf38f6ee1f
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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