Sodium Sulfide → HCID 44132889, compound

HRID 1916273Notes

Reaction equation

HRID 1916273 reaction equation
Cl[C:2]1[C:3]([C:24]#[N:25])=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][OH:23])=[CH:16][CH:15]=2)[C:5]2[C:10](=[O:11])[NH:9][C:8](=[O:12])[NH:7][C:6]=2[N:13]=1.[S-2:26].[Na+].[Na+].Cl[CH2:30][C:31]1[N:32]=[C:33]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)[S:34][CH:35]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.O.C(#N)C.O>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([C:33]2[S:34][CH:35]=[C:31]([CH2:30][S:26][C:2]3[C:3]([C:24]#[N:25])=[C:4]([C:14]4[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][OH:23])=[CH:18][CH:19]=4)[C:5]4[C:10](=[O:11])[NH:9][C:8](=[O:12])[NH:7][C:6]=4[N:13]=3)[N:32]=2)=[CH:37][CH:38]=1

Participants

8

Reactant 4

HCID 14804Sodium SulfideHCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 58158132HCID 58158132, compound

Product 1

HCID 44132889HCID 44132889, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

100 mg (0.229 mmol) of the compound from Example 11A were dissolved in 0.46 ml of DMF, 21 mg (0.274 mmol) of sodium sulfide were added and the mixture was stirred at RT overnight. 33 mg (0.137 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 23 mg (0.275 mmol) of sodium bicarbonate were then added, and the reaction solution was stirred at RT for 2 h. Water was added to the reaction mixture for further purification via a preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA) purified.

Workup

  1. stirringthe reaction solution was stirred at RT for 2 h
  2. custompurified

Sources & evidence

ORD record
ord-36f7a39faecd46b7a38804c73953e0d4
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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