1,1'-Carbonyldiimidazole → 3-{9-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthen-3-yl}-4H-[1,2,4]oxadiazol-5-one

HRID 1987944Notes

Reaction equation

HRID 1987944 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[C:19]3[CH2:25][CH:24]4[N:26]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH:21]([CH2:22][CH2:23]4)[CH2:20]3)[C:10]3[C:15]([O:16][C:17]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[NH:4].[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34]>O1CCOCC1>[F:30][C:28]([F:31])([F:29])[C:27]([N:26]1[CH:21]2[CH2:22][CH2:23][CH:24]1[CH2:25][C:19](=[C:9]1[C:8]3[CH:7]=[CH:6][C:5]([C:3]4[NH:4][C:33](=[O:34])[O:1][N:2]=4)=[CH:18][C:17]=3[O:16][C:15]3[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:20]2)=[O:32]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178513222HCID 178513222, compound

Product 1

HCID 1359999783-{9-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthen-3-yl}-4H-[1,2,4]oxadiazol-5-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of compound 6a (0.1 g, 0.23 mmol) in 1,4-dioxane (4 mL) was added 1,1′-carbonyldiimidazole (CDl, 0.055 g, 0.34 mmol). The mixture was stirred at 110° C. for 40 min under a nitrogen atmosphere. After being cooled, the reaction was concentrated. The crude compound 6b was used in the next reaction without further purification. MS m/z (MH+) 469.8.

Workup

  1. temperatureAfter being cooled
  2. concentrationthe reaction was concentrated
  3. customThe crude compound 6b was used in the next reaction without further purification

Sources & evidence

ORD record
ord-eedb3b00a2ee421bbfa73034b6e9eced
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

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