HCID 86630875, compound → 4,5-Diamino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methylbiphenyl-3-carbonitrile
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]2[CH2:15][CH2:14][C@H:13]([N:16]([CH3:18])[CH3:17])[CH2:12]2)[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:25])[C:3]=1[C:26]#[N:27]>O.O.O.O.O.O.[Fe](Cl)Cl.[Zn].CN(C)C=O>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([N:11]2[CH2:15][CH2:14][C@H:13]([N:16]([CH3:17])[CH3:18])[CH2:12]2)[C:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:25])[C:3]=1[C:26]#[N:27]Participants
Procedure
An aqueous solution (14 ml) of iron chloride hexahydrate (0.83 g, 3.06 mmol) and zinc (5.01 g, 76.6 mmol) were added to an N,N-dimethylformamide (35 ml) solution of 4-amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methyl-5-nitrobiphenyl-3-carbonitrile (I-268) (1.40 g, 3.83 mmol), followed by stirring at room temperature for 1 hour. The insoluble matter was removed by filtration under suction, then the filtrate was diluted with ethyl acetate, washed with aqueous saturated sodium carbonate solution and saturated brine in that order, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, followed by drying with a vacuum pump to obtain the entitled compound (1.25 g, 97%) as a dark brown solid.
Workup
- customThe insoluble matter was removed by filtration under suction
- additionthe filtrate was diluted with ethyl acetate
- washwashed with aqueous saturated sodium carbonate solution and saturated brine in that order
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated away under reduced pressure
- customby drying with a vacuum pump
Sources & evidence
- ORD record
- ord-1a0f2bcf5dc94f82a80cbefce8556a45
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737166B2
Reaction notes
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