Chloroacetyl chloride → HCID 11609724, compound

HRID 1991458Notes

Reaction equation

HRID 1991458 reaction equation
[OH:1][NH:2][C:3](=[NH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.Cl[CH2:21][C:22](Cl)=O.C([O-])([O-])=O.[K+].[K+].[SH:31][C:32]1[N:39]=[C:38]([CH3:40])[C:37]([CH3:41])=[C:36]([CH3:42])[C:33]=1[C:34]#[N:35]>C(Cl)Cl.O.CN(C=O)C.C1(C)C=CC=CC=1>[CH3:42][C:36]1[C:37]([CH3:41])=[C:38]([CH3:40])[N:39]=[C:32]2[S:31][C:22]([C:21]3[O:1][N:2]=[C:3]([C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[N:10]=3)=[C:34]([NH2:35])[C:33]=12

Participants

10

Reactant 5

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 178433545HCID 178433545, compoundHCID 178513281HCID 178513281, compound

Product 1

HCID 11609724HCID 11609724, compoundYield 21%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-hydroxy-benzamidine (41 mg, 0.30 mmol) in DCM (10 mL) was added PS-DIEA (240 mg, 0.90 mmol), followed by the addition of chloroacetyl chloride (0.36 mL, 0.45 mmol). The mixture was shaken at room temperature for 24 hr and filtered to remove the resin. The solvent was then replaced with toluene and the mixture obtained was stirred at 120° C. in a sealed tube overnight. The toluene was then replaced with DMF (10 mL) and to the solution was added K2CO3 (124 mg, 0.90 mmol) and 2-mercapto-4,5,6-trimethyl-nicotinonitrile (54 mg, 0.30 mmol). The mixture was stirred at 80° C. overnight before pouring it into water. The precipitate was collected and purified via flash chromatography to provide the title product, 4,5,6-trimethyl-2-(3-phenyl-[1,2,4]oxadiazol-5-yl)-thieno[2,3-b]pyridin-3-yl amine (21 mg, 21%).

Workup

  1. filtrationfiltered
  2. customto remove the resin
  3. customthe mixture obtained
  4. stirringwas stirred at 120° C. in a sealed tube overnight
  5. stirringThe mixture was stirred at 80° C. overnight
  6. customThe precipitate was collected
  7. custompurified via flash chromatography

Sources & evidence

ORD record
ord-68f76a97373c4708bc5693c9f9a5455f
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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