Triethylamine → HCID 178461763, compound

HRID 1670638Notes

Reaction equation

HRID 1670638 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[CH:35]=[C:34]([F:36])[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]([CH3:28])[CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:15]([N+:29]([O-])=O)[CH:14]=1.C(N(CC)CC)C.C1C=CC(O[C:52](OC2C=CC=CC=2)=[N:53][C:54]#[N:55])=CC=1>O1CCCC1.C(O)(C)C.[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[CH:35]=[C:34]([F:36])[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]([CH3:28])[CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)/[C:52](=[N:53]/[C:54]#[N:55])/[NH:29][C:15]=2[CH:14]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 57748733(R)-[4-((E)-3,8-Difluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-2-nitro-phenyl]-(1-methyl-2-morpholin-4-yl-ethyl)-amine

Product 1

HCID 178461763HCID 178461763, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (R)-[4-((E)-3,8-difluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-2-nitro-phenyl]-(1-methyl-2-morpholin-4-yl-ethyl)-amine (0.017 mol, 9.0 g) in tetrahydrofuran (35 mL) and isopropanol (90 mL). Add triethylamine (0.039 mol, 3.9) and 10% platinum on carbon (1.5 g) and hydrogenate in a Parr shaker at 50 psi (H2) at room temperature for 2 h. Filter off the catalyst through a plug of diatomaceous earth. Dilute the filtrate with dioxane (35 mL), add diphenyl N-cyanocarbonimidate (0.019 mol, 4.61 g) and stir at room temperature for 48 h. Concentrate the reaction mixture under reduced pressure. Purify on a silica gel column using 0.5% methanol in dichloromethane as eluent to obtain the title compound (6.0 g, 64%) as an off-white solid. LC-MS m/z 528.2 [M+H]+.

Workup

  1. filtrationFilter off the catalyst through a plug of diatomaceous earth
  2. additionDilute the filtrate with dioxane (35 mL)
  3. concentrationConcentrate the reaction mixture under reduced pressure
  4. customPurify on a silica gel column

Sources & evidence

ORD record
ord-5364068466364468914e85405b962fa0
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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