Tributylphosphine → HCID 66960684, compound

HRID 68987Notes

Reaction equation

HRID 68987 reaction equation
C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[N+:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[S:41]([NH:44][CH2:45][CH2:46][N:47]1[CH:56]=[CH:55][C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:48]1=[O:57])(=[O:43])=[O:42])([O-:34])=[O:33].[CH2:58]([N:60]1[C:66](=[O:67])[C:65]([CH3:69])([CH3:68])[C:64](=[O:70])[N:63]([CH3:71])[C:62]2[CH:72]=[C:73]([CH2:76][CH2:77][CH2:78]O)[CH:74]=[CH:75][C:61]1=2)[CH3:59]>O.C1(C)C=CC=CC=1>[CH2:58]([N:60]1[C:66](=[O:67])[C:65]([CH3:69])([CH3:68])[C:64](=[O:70])[N:63]([CH3:71])[C:62]2[CH:72]=[C:73]([CH2:76][CH2:77][CH2:78][N:44]([CH2:45][CH2:46][N:47]3[CH:56]=[CH:55][C:54]4[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:48]3=[O:57])[S:41]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[N+:32]([O-:34])=[O:33])(=[O:42])=[O:43])[CH:74]=[CH:75][C:61]1=2)[CH3:59]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 669613052-nitro-N-[2-(1-oxo-1H-isoquinolin-2-yl)-ethyl]-benzenesulfonamideHCID 706568861-Ethyl-7-(3-hydroxy-propyl)-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 66960684HCID 66960684, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Tributyl phosphine (1.2 ml) and 1,1′-(azodicarbonyl)dipiperidine (1.17 g) were added to a toluene solution (100 ml) of 2-nitro-N-[2-(1-oxo-1H-isoquinolin-2-yl)-ethyl]-benzenesulfonamide (1.39 g), and 1-ethyl-7-(3-hydroxy-propyl)-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione (0.94 g). The mixture was stirred overnight. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was washed with water and saturated saline, dried with magnecium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1→1:0). The purified product was condensed under reduced pressure to produce the title compound (0.54 g) as a white amorphous.

Workup

  1. extractionfollowed by extraction
  2. washThe organic layer was washed with water and saturated saline
  3. dry with materialdried with magnecium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1→1:0)
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-28b9692ca7a34b9c8b991784b78aa794
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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