Pyridine → HCID 59835867, compound

HRID 1916770Notes

Reaction equation

HRID 1916770 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:22]=[CH:23][C:24]([O:28][CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[C:25]([NH2:27])[CH:26]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:22]=[CH:23][C:24]([O:28][CH2:29][CH2:30][N:31]4[CH2:32][CH2:33][CH2:34][CH2:35]4)=[C:25]([NH:27][S:2]([CH3:1])(=[O:4])=[O:3])[CH:26]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chloride2×HCID 59835738HCID 59835738, compound

Product 1

HCID 59835867HCID 59835867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an N2 atmosphere 39 μL (0.5 mmol) methanesulphonic acid chloride are added to a solution of 100 mg (0.24 mmol) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-phenylamine and 161 μL (2 mmol) pyridine in 10 mL DCM and the reaction mixture is stirred for 2 h at RT. To complete the reaction a further 160 μL pyridine and 39 μL methanesulphonic acid chloride are added and the mixture is stirred overnight. It is combined with 10% Na2CO3 solution, the organic phase is separated off and the solvent is eliminated i.vac. The residue is purified by HPLC.

Workup

  1. additionare added
  2. stirringthe mixture is stirred overnight
  3. customthe organic phase is separated off
  4. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-82a2b8aaaa23411ca5da1fd54b62599f
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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