4-Bromo-2-methylaniline → HCID 67380949, compound

HRID 1804086Notes

Reaction equation

HRID 1804086 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.Cl[CH2:11][CH2:12][N:13]([CH2:24][CH2:25]Cl)S(C1C=CC(C)=CC=1)(=O)=O.[CH:27]1(B(O)O)[CH2:29][CH2:28]1>>[CH:27]1([C:2]2[CH:8]=[CH:7][C:5]([N:6]3[CH2:11][CH2:12][NH:13][CH2:24][CH2:25]3)=[C:4]([CH3:9])[CH:3]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 3

HCID 114234-Bromo-2-methylanilineHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 2760897Cyclopropylboronic acid

Product 1

HCID 67380949HCID 67380949, compoundYield 35.2%

Procedure

By reaction and treatment in the same manner as in Preparation Example 15 and using 4-bromo-2-methylaniline (3 g), N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide (5.65 g) and cyclopropylboronic acid (721 mg), 1-(4-cyclopropyl-2-methylphenyl)piperazine (640 mg) was obtained. To a solution (7 mL) of 6-bromonicotinic acid (132 mg) in methanol were added 1-(4-cyclopropyl-2-methylphenyl)piperazine (150 mg) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (217 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (ethyl acetate:hexane) to give the title compound (260 mg).

Workup

  1. customBy reaction and treatment in the same manner
  2. customas in Preparation Example 15

Sources & evidence

ORD record
ord-55ff69408e3a46e0a701ee1e91161f0d
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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