Pyridine → 4-chloro-N-(4-methyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)phenyl)benzenesulfonamide

HRID 1361656Notes

Reaction equation

HRID 1361656 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][N:17]=2)=[CH:14][CH:13]=[CH:12][N:11]=1.N1C=CC=CC=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>C(Cl)Cl>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:9][C:10]3[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][N:17]=4)=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:4]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 583962724-methyl-N3-(3-pyrimidin-4-yl-pyridin-2-yl)-benzene-1,3-diamine

Product 1

HCID 585883494-chloro-N-(4-methyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)phenyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-N3-(3-pyrimidin-4-yl-pyridin-2-yl)-benzene-1,3-diamine (40 mg, 0.14 mmol) in CH2Cl2 (2.5 mL) was added pyridine (0.012 mL, 0.14 mmol) and 4-chlorobenzenesulfonyl chloride (30 mg, 0.14 mmol). The mixture was stirred overnight at RT, concentrated and purified by flash chromatography (0→50% EtOAc/n-Hexanes) to yield 4-chloro-N-(4-methyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)phenyl)benzenesulfonamide. MS m/z=452 [M+1]+. Calc'd for C22H18ClN5O2S: 451.94.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography (0→50% EtOAc/n-Hexanes)

Sources & evidence

ORD record
ord-2d2acbf865ae450c823e526565ae71f1
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

Loading…