Dimethyl Sulfoxide → 2-Amino-5-bromo-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methyl-3-nitrobenzonitrile

HRID 17552Notes

Reaction equation

HRID 17552 reaction equation
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.CS(C)=O.[NH2:13][C:14]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20](F)[C:19]([Br:26])=[C:18]([CH3:27])[C:15]=1[C:16]#[N:17].C(N(CC)CC)C>O>[NH2:13][C:14]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20]([N:5]2[CH2:6][CH2:7][C@H:3]([N:2]([CH3:8])[CH3:1])[CH2:4]2)[C:19]([Br:26])=[C:18]([CH3:27])[C:15]=1[C:16]#[N:17]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 860973752-Amino-5-bromo-4-fluoro-6-methyl-3-nitrobenzonitrile

Product 1

HCID 866308742-Amino-5-bromo-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methyl-3-nitrobenzonitrileYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (140 μl, 1.10 mmol) was added to a dimethyl sulfoxide (2 ml) solution of 2-amino-5-bromo-4-fluoro-6-methyl-3-nitrobenzonitrile (I-266) (274 mg, 1.00 mmol) and triethylamine (209 μl, 1.50 mmol), followed by stirring at room temperature for 30 minutes. The reaction liquid was poured into water, and the precipitated solid was collected by filtration, washed with water, and dried to obtain the entitled compound (359 mg, 97%) as a yellow solid.

Workup

  1. customThe reaction liquid
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3997e68c0e2946a1818e4ab2172121e9
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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