Bis-(1H-imidazol-2-YL)-methanone → HCID 25007104, compound

HRID 1436475Notes

Reaction equation

HRID 1436475 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:13][CH:14]3[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C:20](=[O:22])[CH:17]4[CH2:18][CH2:19][CH:14]3[CH2:15][CH2:16]4)[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 86618626HCID 86618626, compound

Product 1

HCID 25007104HCID 25007104, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A portion of 4-[4-(4-Bromo-phenyl)-thiazol-2-ylamino]-cyclohexanecarboxylic acid (50 mg, 0.13 mmol) was dissolved in dioxane (10 mL). Carbonyl diimidazole (26 mg, 0.16 mmol) was added and the mixture was heated to 100° C. for 16 h. The mixture was concentrated and chromatographed with 10% acetone in hexane to give 32 mg of 2-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2-azabicyclo[2.2.2]octan-3-one.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed with 10% acetone in hexane

Sources & evidence

ORD record
ord-af11b10665f94ee58db070f7fb717a0a
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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