Ethanesulfonyl chloride → n-(1-(5-(3-Chloro-4-cyanophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamide

HRID 2407441Notes

Reaction equation

HRID 2407441 reaction equation
[NH2:1][C:2]1([C:5]2[CH:6]=[C:7]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([Cl:19])[CH:12]=3)[CH:8]=[N:9][CH:10]=2)[CH2:4][CH2:3]1.[CH2:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21]>C(Cl)Cl>[Cl:19][C:13]1[CH:12]=[C:11]([C:7]2[CH:6]=[C:5]([C:2]3([NH:1][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[CH2:3][CH2:4]3)[CH:10]=[N:9][CH:8]=2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 595784184-(5-(1-Aminocyclopropyl)pyridin-3-yl)-2-chlorobenzonitrile

Product 1

HCID 49821054n-(1-(5-(3-Chloro-4-cyanophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-(1-aminocyclopropyl)pyridin-3-yl)-2-chlorobenzonitrile (70 mg, 0.26 mmol) in DCM (3 mL) at room temperature was added TEA (0.109 mL, 0.779 mmol) and EtSO2Cl (74 μL, 0.779 mmol) dropwise, and the mixture was stirred at room temperature for 1 h. The mixture was concentrated in vacuo, re-dissolved in DMF (3 mL) and filtered. The filtrate was purified by Xbridge Phenyl followed by Xbridge C18 eluting with 20-80% ACN-water gradient to give N-(1-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamide. HRMS: (ESI) m/z 362.0712 [(M+H)+ Calcd for C17H16ClN3O2S 362.0725]. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.28 (t, J=7.3 Hz, 3H), 1.32-1.38 (m, 2H), 1.49-1.54 (m, 2H), 2.90 (q, J=7.4 Hz, 2H), 7.60 (dd, J=8.1, 1.8 Hz, 1H), 7.74 (d, J=1.8 Hz, 1H), 7.79 (d, J=8.1 Hz, 1H), 8.01 (t, J=2.3 Hz, 1H), 8.67 (d, J=2.3 Hz, 1H), 8.72 (d, J=2.3 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionre-dissolved in DMF (3 mL)
  3. filtrationfiltered
  4. customThe filtrate was purified by Xbridge Phenyl
  5. washC18 eluting with 20-80% ACN-water gradient

Sources & evidence

ORD record
ord-aa3e99f5400c4b0f99dca8d29bf2ee21
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Reaction notes

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