Water → HCID 58484486, compound

HRID 1804087Notes

Reaction equation

HRID 1804087 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]1([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[C:16]([CH3:26])[CH:15]=2)[CH2:13][CH2:12]1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.O>CO>[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:23]2[CH2:24][CH2:25][N:20]([C:17]3[CH:18]=[CH:19][C:14]([CH:11]4[CH2:13][CH2:12]4)=[CH:15][C:16]=3[CH3:26])[CH2:21][CH2:22]2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2389326-Bromonicotinic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 67380949HCID 67380949, compound

Product 1

HCID 58484486HCID 58484486, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-af69dc93367c43dabdcb6963f05d9bf9
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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