Oxalyl chloride → HCID 57864392, compound

HRID 1672686Notes

Reaction equation

HRID 1672686 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:11]1[CH:47]=[CH:46][C:14]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2/[CH:23]=[CH:24]/[CH:25]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=2)[CH2:26][CH2:27][C:28]2[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=2)=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[NH2:48][NH:49][C:50]([NH2:52])=[S:51]>C1COCC1.CN(C=O)C>[C:7]([C:11]1[CH:47]=[CH:46][C:14]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2/[CH:23]=[CH:24]/[CH:25]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=2)[CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:32]([NH:48][NH:49][C:50](=[S:51])[NH2:52])=[O:33])=[CH:35][CH:36]=2)=[CH:13][CH:12]=1)([CH3:8])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 2723789ThiosemicarbazideHCID 57864399HCID 57864399, compound

Product 1

HCID 57864392HCID 57864392, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

5.9 mg (0.05 mmol) of oxalyl chloride are slowly added dropwise to a solution of 12.7 mg (0.02 mmol) of 4-[(4E)-5-{2-[(4-tert-butylbenzyl)oxy]phenyl}-3-(4-cyanobenzyl)pent-4-en-1-yl]-benzoic acid from Example 100A in 0.2 ml of dry THF with 1 drop of DMF while cooling in ice. The reaction mixture is stirred at RT for 30 minutes and then concentrated in vacuo, and the residue is coevaporated twice with dichloromethane and then taken up in 0.2 ml of THF. This solution is added dropwise to a solution of 4.2 mg (0.05 mmol) of thiosemicarbazide in 0.25 ml of THF at 0° C. The mixture is stirred at RT for 1 hour and then concentrated, and the residue is reacted without further purification in the next stage.

Workup

  1. temperaturewhile cooling in ice
  2. concentrationconcentrated in vacuo
  3. stirringThe mixture is stirred at RT for 1 hour
  4. concentrationconcentrated
  5. customthe residue is reacted without further purification in the next stage

Sources & evidence

ORD record
ord-de6a994159db407b9057de57b8d9d1b3
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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