4-Chloroaniline → HCID 16050422, compound

HRID 2235126Notes

Reaction equation

HRID 2235126 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](O)=[O:21])[CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.CN1CCOCC1.N1C(Cl)=NC(Cl)=NC=1Cl.[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=1>CC(C)=O>[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:20]([C:17]2[CH:18]=[C:19]3[C:14]([CH2:13][CH2:12][N:11]3[S:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:23][CH3:24])(=[O:10])=[O:9])=[CH:15][CH:16]=2)=[O:21])=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 7954Cyanuric chlorideHCID 79724-MethylmorpholineHCID 68432545HCID 68432545, compound

Product 1

HCID 16050422HCID 16050422, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (30 mg, 0.082 mmol) in acetone (0.9 ml) was treated with N-methylmorpholine (0.025 ml, 2.4 equiv.) and cyanuric chloride (18 mg, 0.098 mmol, 1.2 equiv.) and stirred at room temperature for 2 hours. 4-Chloro-phenyl-amine (12 mg, 0.098 mol, 1.2 equiv.) was then added, and the mixture was stirred for 12 hours at room temperature. The solvent was evaporated, and the residue dissolved in methanol (2.5 ml) and purified by preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid). 1-(5-Chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-chloro-phenyl)-amide was obtained as a white solid, 10.6 mg (27%). MS (ISP): m/e=474.9, 477.8 (M−H), δH (300 MHz; d6-DMSO) 10.33 (1H, s), 7.86 (1H, d), 7.79 (2H, d), 7.71 (1H, s), 7.69 (1H, d), 7.60 (1H, d), 7.40 (2H, d), 7.35 (1H, d), 7.21 (1H, d), 4.10 (2H, t), 3.66 (3H, s), 3.12 (2H, t).

Workup

  1. stirringthe mixture was stirred for 12 hours at room temperature
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in methanol (2.5 ml)
  4. custompurified by preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid)

Sources & evidence

ORD record
ord-b956a24b36cd4ea2afe10911ff5a37a1
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

Loading…