Triethylamine → HCID 10048913, compound

HRID 1916648Notes

Reaction equation

HRID 1916648 reaction equation
CS(Cl)(=O)=O.[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]4[O:28][C:27]([CH2:29]O)=[CH:26][C:25]=4[CH:31]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C.[CH3:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>C(Cl)Cl.O>[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]4[O:28][C:27]([CH2:29][N:43]5[CH2:44][CH2:45][CH:40]([CH3:39])[CH2:41][CH2:42]5)=[CH:26][C:25]=4[CH:31]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 693814-MethylpiperidineHCID 67363469HCID 67363469, compound

Product 1

HCID 10048913HCID 10048913, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

32 μL (0.40 mmol) methanesulphonic acid chloride are added to a solution of 100 mg (0.28 mmol) {5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-benzofuran-2-yl}-methanol and 69 μL (0.50 mmol) triethylamine in 5 mL DCM at 0° C. and the reaction is stirred for 1 h at this temperature. Another 70 μL (0.89 mmol) methanesulphonic acid chloride are added and the reaction is stirred overnight at RT. Then 0.24 ml (2.00 mmol) 4-methylpiperidine is added and the reaction is stirred for 2 hours at RT. The reaction solution is diluted with water and the aqueous phase extracted twice with DCM. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (DCM/methanol 9:1).

Workup

  1. stirringthe reaction is stirred overnight at RT
  2. stirringthe reaction is stirred for 2 hours at RT
  3. extractionthe aqueous phase extracted twice with DCM
  4. dry with materialThe organic phase is dried over MgSO4
  5. customThe purification

Sources & evidence

ORD record
ord-9b6e8c4d2a524524bbdfcb8491fc7c25
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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