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N,N,N',N'-Tetramethylazodicarboxamide → N-(3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl)-N-(2-(7-methyl-1-oxo-1H-isoquinolin-2-yl)ethyl)-2-nitrobenzenesulfonamide

HRID 2196083
Notes
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Reaction equation

HRID 2196083 reaction equation
CN(C)C(N=NC(N(C)C)=O)=O.C(P(CCCC)CCCC)CCC.[CH2:26]([N:28]1[C:34](=[O:35])[C:33]([CH3:37])([CH3:36])[C:32](=[O:38])[N:31]([CH3:39])[C:30]2[CH:40]=[C:41]([O:44][CH2:45][CH2:46][CH2:47][NH:48][S:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[N+:58]([O-:60])=[O:59])(=[O:51])=[O:50])[CH:42]=[CH:43][C:29]1=2)[CH3:27].O[CH2:62][CH2:63][N:64]1[CH:73]=[CH:72][C:71]2[C:66](=[CH:67][C:68]([CH3:74])=[CH:69][CH:70]=2)[C:65]1=[O:75]>ClCCl.O.C1COCC1>[CH2:26]([N:28]1[C:34](=[O:35])[C:33]([CH3:37])([CH3:36])[C:32](=[O:38])[N:31]([CH3:39])[C:30]2[CH:40]=[C:41]([O:44][CH2:45][CH2:46][CH2:47][N:48]([CH2:62][CH2:63][N:64]3[CH:73]=[CH:72][C:71]4[C:66](=[CH:67][C:68]([CH3:74])=[CH:69][CH:70]=4)[C:65]3=[O:75])[S:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[N+:58]([O-:60])=[O:59])(=[O:51])=[O:50])[CH:42]=[CH:43][C:29]1=2)[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 68672787N-(3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl)-2-nitrobenzenesulfonamideHCID 686736362-(2-hydroxyethyl)-7-methyl-2H-isoquinolin-1-one

Product 1

HCID 68672764
N-(3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl)-N-(2-(7-methyl-1-oxo-1H-isoquinolin-2-yl)ethyl)-2-nitrobenzenesulfonamide
Yield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N,N,N′,N′-Tetra methyl azodicarboxamide (TMAD) (118 mg) and tri-n-butyl phosphine (0.17 ml) were added to a THF solution (5 ml) of N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]-2-nitrobenzenesulfonamide (231 mg) and 2-(2-hydroxyethyl)-7-methyl-2H-isoquinolin-1-one (93 mg), and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→10:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 205 mg (yield: 65%) of N-(3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl)-N-(2-(7-methyl-1-oxo-1H-isoquinolin-2-yl)ethyl)-2-nitrobenzenesulfonamide as a white amorphous solid.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→10:1)
  4. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-94b8e8248eb5448984a03de9e73b1259
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08338406B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes