Dimethylformamide → HCID 117699036, compound

HRID 1049800Notes

Reaction equation

HRID 1049800 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[C:9]3[C:14]([CH:15]=[CH:16][C:6]=2[N:5]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[N+:33]([O-:35])=[O:34])(=[O:26])=[O:25])=[CH:19][CH:18]=2)[C:4](=[O:36])[CH2:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.CN(C)C=O.[C:42](=[O:45])([O-])[O-].[K+].[K+].[CH2:48](Br)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>O>[CH2:48]([N:23]([C:20]1[CH:21]=[CH:22][C:17]([N:5]2[C:4](=[O:36])[CH2:3][C:42](=[O:45])[N:8]([CH2:2][C:6]3[CH:16]=[CH:15][CH:14]=[CH:9][CH:7]=3)[C:7]3[C:9]4[C:14]([CH:15]=[CH:16][C:6]2=3)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:18][CH:19]=1)[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34])(=[O:26])=[O:25])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.[CH2:48]([N:23]([C:20]1[CH:21]=[CH:22][C:17]([N:5]2[C:4](=[O:36])[CH2:3][C:2](=[O:1])[NH:8][C:7]3[C:9]4[C:14]([CH:15]=[CH:16][C:6]2=3)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:18][CH:19]=1)[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34])(=[O:26])=[O:25])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 117699060HCID 117699060, compound

Product 2

HCID 117699008HCID 117699008, compoundYield 31%HCID 117699036HCID 117699036, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-[4-(2,4-Dioxo-1,2,3,4-tetrahydronaphtho[1,2-b][1,4]diazepin-5-yl)phenyl]-2-nitrobenzenesulfonamide (110 mg, 0.22 mmol) obtained in Example 145, dimethylformamide (1 mL), potassium carbonate (91 mg, 0.66 mmol), and benzyl bromide (31 μL, 0.26 mmol) were mixed, and the mixture was stirred at room temperature for 2 hours and 30 minutes. This reaction mixture was added with water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 3/2) to give N-benzyl-N-[4-(1-benzyl-2,4-dioxo-1,2,3,4-tetrahydronaphtho[1,2-b][1,4]diazepin-5-yl)phenyl]-2-nitrobenzenesulfonamide (47 mg, yield 31%) as white amorphous, and N-benzyl-N-[4-(2,4-dioxo-1,2,3,4-tetrahydronaphtho[1,2-b][1,4]diazepin-5-yl)phenyl]-2-nitrobenzenesulfonamide (54 mg, yield 41%) as white amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 3/2)

Sources & evidence

ORD record
ord-e47692e835cb4ebb92fb1a3c7b4f8c52
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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