(2-Chlorophenyl)methanesulfonyl chloride → HCID 49818969, compound

HRID 1897761Notes

Reaction equation

HRID 1897761 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([Cl:16])[CH:9]=2)[CH:5]=[N:6][CH:7]=1.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[Cl:16][C:10]1[CH:9]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][S:25]([CH2:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[Cl:17])(=[O:26])=[O:27])[CH:7]=[N:6][CH:5]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 2757801(2-Chlorophenyl)methanesulfonyl chlorideHCID 595783904-(5-Amino-pyridin-3-yl)-2-chloro-benzonitrile

Product 1

HCID 49818969HCID 49818969, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

According to General Sulfonylation Procedure 2 in Example 1, to a solution of 4-(5-amino-pyridin-3-yl)-2-chloro-benzonitrile (20 mg, 87 μmol, 1 eq) in anhydrous pyridine (500 μl) was added (2-chloro-phenyl)-methanesulfonyl chloride (21.6 mg, 96 μmol, 1.1 eq). The crude product was purified by Isco Cornbiflash® Companion™ flash chromatography system on normal phase (4 g SiO2, flow rate 18 mL/min), eluting with mixtures of dichloromethane/methanol, to give N-[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-1-(2-chloro-phenyl)-methanesulfonamide (15.1 mg, >95% purity, yield: 41.5%). The isolated product was lyophilized and identified by LC-MS (system 1) and NMR (system 2): ESI-MS m/z: 418 [M+H]+, retention time=2.34 min, 1H NMR (400 MHz, DMSO-d6) δ ppm 4.80 (s, 2H) 7.30-7.32 (m, 2H) 7.37-7.39 (m, 1H) 7.47-7.49 (m, 1H) 7.69 (t, J=2.27 Hz, 1H) 7.75 (dd, J=8.08, 1.77 Hz, 1H) 7.98 (d, J=1.77 Hz, 1H) 8.09 (d, J=8.08 Hz, 1H) 8.37 (d, J=2.53 Hz, 1H) 8.61 (d, J=1.89 Hz, 1H) 10.50 (br. s., 1H).

Workup

  1. customThe crude product was purified by Isco Cornbiflash® Companion™ flash chromatography system on normal phase (4 g SiO2, flow rate 18 mL/min)
  2. washeluting with mixtures of dichloromethane/methanol

Sources & evidence

ORD record
ord-b9ff7c8b882c4db888803b8d58f8e9a1
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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