Sodium Hydroxide → HCID 178440942, compound

HRID 1672691Notes

Reaction equation

HRID 1672691 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]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=2)[CH2:26][C:27]2[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=2)=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[C:48]([NH:51][NH2:52])([NH2:50])=[NH:49].Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.CN(C=O)C.C1COCC1.O>[C:7]([C:11]1[CH:12]=[CH:13][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]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=2)[CH2:26][C:27]2[CH:35]=[CH:34][C:30]([C:31]([NH:52][NH:51][C:48](=[NH:49])[NH2:50])=[O:32])=[CH:29][CH:28]=2)=[CH:46][CH:47]=1)([CH3:8])([CH3:9])[CH3:10]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 578644144-{(3E)-4-{2-[(4-tert-Butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoic acidHCID 178418668HCID 178418668, compound

Product 1

HCID 178440942HCID 178440942, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

210 mg (1.66 mmol) of oxalyl chloride are slowly added dropwise to a solution of 150 mg (0.28 mmol) of 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoic acid from Example 105A in 1.5 ml of dry toluene with 2 drops of DMF while cooling in ice. The reaction mixture is stirred at RT for 5 minutes and then heated to reflux for 1 hour. After cooling, the mixture is concentrated in vacuo, and the residue is coevaporated twice with toluene and then taken up in 3 ml of THF. This solution is added to a previously prepared solution of 33.5 mg (0.30 mmol) of aminoguanidine hydrochloride and 22 mg (0.55 mmol) of sodium hydroxide in 1 ml of THF and 0.25 ml of water at 0° C. The mixture is stirred at 0° C. for 2 hours and then concentrated, and the residue is reacted without further purification in the next stage.

Workup

  1. temperaturewhile cooling in ice
  2. temperatureheated
  3. temperatureto reflux for 1 hour
  4. temperatureAfter cooling
  5. concentrationthe mixture is concentrated in vacuo
  6. stirringThe mixture is stirred at 0° C. for 2 hours
  7. concentrationconcentrated
  8. customthe residue is reacted without further purification in the next stage

Sources & evidence

ORD record
ord-2547802ccc534e8fa08679cfd1892aae
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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