Pyridine → HCID 178512083, compound

HRID 1670644Notes

Reaction equation

HRID 1670644 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:37]=1)[O:7][CH2:8][C:9]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C@@H:20]2[CH2:28][N:27]3[C@H:22]([CH2:23][O:24][CH2:25][CH2:26]3)[CH2:21]2)=[C:15]([N+:29]([O-])=O)[CH:14]=1.C(N(CC)CC)C.N1C=CC=CC=1.C1C=CC(O[C:58](OC2C=CC=CC=2)=[N:59][C:60]#[N:61])=CC=1>O1CCCC1.[Pt]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:37]=1)[O:7][CH2:8][C:9]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]2[N:19]([C@@H:20]3[CH2:28][N:27]4[C@H:22]([CH2:23][O:24][CH2:25][CH2:26]4)[CH2:21]3)/[C:58](=[N:59]/[C:60]#[N:61])/[NH:29][C:15]=2[CH:14]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 57748742HCID 57748742, compound

Product 1

HCID 178512083HCID 178512083, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve [4-((E)-3,7-difluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-2-nitro-phenyl]-((7S,8aS)-hexahydro-pyrrolo[2,1-c][1,4]oxazin-7-yl)-amine (0.009 mol, 5.0 g) in tetrahydrofuran (40 mL). Add triethylamine (0.009 mol, 0.9 g) and 10% platinum on carbon (1.0 g) and hydrogenate in a Parr shaker at 50 psi (H2) at room temperature for 3 h. Filter off the catalyst through a plug of diatomaceous earth, add pyridine (40 mL) and diphenyl N-cyanocarbonimidate (0.009 mol, 2.35 g) to the filtrate. Stir at room temperature for 16 h, then heat at 60-70° C. for 8 h. Remove the solvent under reduced pressure. Dissolve the resulting 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 on a silica gel column using 1% methanol in dichloromethane as eluent to give the title compound (1.9 g, 36%). LC-MS m/z 526.4 [M+H]+.

Workup

  1. filtrationFilter off the catalyst through a plug of diatomaceous earth
  2. temperatureheat at 60-70° C. for 8 h
  3. customRemove the solvent under reduced pressure
  4. dissolutionDissolve the resulting 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 on a silica gel column

Sources & evidence

ORD record
ord-4497e23b06134d84963570bd684f54d9
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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