Triethylamine → HCID 178480576, compound

HRID 1670642Notes

Reaction equation

HRID 1670642 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:33]=1)[O:7][CH2:8][C:9]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH:20]2[CH2:23][N:22]([CH3:24])[CH2:21]2)=[C:15]([N+:25]([O-])=O)[CH:14]=1.C(N(CC)CC)C.C1C=CC(O[C:48](OC2C=CC=CC=2)=[N:49][C:50]#[N:51])=CC=1>O1CCCC1.[Pt].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:33]=1)[O:7][CH2:8][C:9]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:10]=1/[C:11]/2=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]2[N:19]([CH:20]3[CH2:23][N:22]([CH3:24])[CH2:21]3)/[C:48](=[N:49]/[C:50]#[N:51])/[NH:25][C:15]=2[CH:14]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 57748783HCID 57748783, compound

Product 1

HCID 178480576HCID 178480576, compoundYield 151.1%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve [4-((E)-3,7-difluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-2-nitro-phenyl]-(1-methyl-azetidin-3-yl)-amine (4.23 mmol, 1.90 g), triethylamine (9.31 mmol, 1.30 mL) in tetrahydrofuran (20 mL), add 5% platinum on carbon (200 mg) and hydrogenate (50 psi) at 35° C. for one hour. Filter off the catalyst, rinse with pyridine (20 mL), add diphenyl N-cyanocarbonimidate (4.65 mmol, 1.11 g) and stir at room temperature overnight under nitrogen. Dilute with ethyl acetate, wash with 5% aqueous sodium bicarbonate twice, dry over anhydrous sodium sulfate, filter, and concentrate in vacuo to obtain approximately 3 g of an orange oil. Purify on an 80 g silica gel column eluting with 5% methanol in dichloromethane to obtain ˜930 mg of a yellow semi-solid. Dissolve in a minimum amount of methanol and let sit. White solids form. After 30 min filter off the solids and rinse with methanol to obtain the title compound as a white solid (815 mg, 41%). LC-MS m/z 470.2 [M+H]+.

Workup

  1. filtrationFilter off the catalyst
  2. washrinse with pyridine (20 mL)
  3. washwash with 5% aqueous sodium bicarbonate twice
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b74ed16147ca473498693a0481e2c981
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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