HCID 15054039, compound → HCID 23046050, compound

HRID 2107532Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([NH2:13])=[O:12])[NH:6]2.[C:14]1([CH:20]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:21]2[CH2:24][CH:23]([O:25][CH2:26][CH:27]3[O:29][CH2:28]3)[CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[OH-].[Na+].O1CCOCC1>[C:30]1([CH:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:21]2[CH2:24][CH:23]([O:25][CH2:26][CH:27]([OH:29])[CH2:28][O:1][C:2]3[CH:10]=[CH:9][CH:8]=[C:7]4[C:3]=3[CH:4]=[C:5]([C:11]([NH2:13])=[O:12])[NH:6]4)[CH2:22]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 60 °C

Procedure

8.8 g of 4-hydroxy-1H-indole-2-carboxamide are dissolved in 250 ml of 0.8 percent strength sodium hydroxide solution and a solution of 16.3 g of 1-(diphenylmethyl)-3-(2,3-epoxypropoxy)azetidine in 250 ml of dioxane is added. The mixture is allowed to stand for 4 hours at room temperature and then warmed to 60° C. for a further 20 hours. The reaction mixture is then stirred into 1 l of ice water and extracted twice with 500 ml of methylene chloride each time. The organic phase is dried using potassium carbonate and the solvent is removed by distillation in vacuo. The residue is triturated twice with 100 ml of diisopropyl ether each time and filtered off with suction.

Workup

extractionextracted twice with 500 ml of methylene chloride each time
customThe organic phase is dried
customthe solvent is removed by distillation in vacuo
customThe residue is triturated twice with 100 ml of diisopropyl ether each time
filtrationfiltered off with suction

Sources & evidence

ORD record: ord-edefa76a539746cda0badd02eb6ba026
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04935414

Reaction notes

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