Cyclopropanesulfonyl chloride → HCID 49819669, compound

HRID 1897763Notes

Reaction equation

HRID 1897763 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.[CH:17]1([S:20](Cl)(=[O:22])=[O:21])[CH2:19][CH2:18]1>N1C=CC=CC=1>[Cl:16][C:10]1[CH:9]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][S:20]([CH:17]3[CH2:19][CH2:18]3)(=[O:22])=[O:21])[CH:7]=[N:6][CH:5]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 595783904-(5-Amino-pyridin-3-yl)-2-chloro-benzonitrile

Product 1

HCID 49819669HCID 49819669, compoundYield 29.3%

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 cyclopropanesulfonyl chloride (9.8 μl, 96 mmol, 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 cyclopropanesulfonic acid [5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-amide (8.5 mg, >95% purity, yield: 29.2%). The isolated product was lyophilized and identified by LC-MS (system 1) and NMR (system 2): ESI-MS m/z: 334 [M+H]+, retention time=1.90 min, 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93-0.99 (m, 4H) 2.80-2.85 (m, 1H) 7.84 (dd, J=8.08, 1.64 Hz, 1H) 7.89 (t, J=2.21 Hz, 1H) 8.08 (d, J=8.08 Hz, 1H) 8.10 (s, 1H) 8.48 (d, J=2.40 Hz, 1H) 8.70 (d, J=1.89 Hz, 1H) 10.15 (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-b5802800af0d437ca663ee6b70626a45
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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