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Diisopropyl Ether → HCID 22492912, compound

HRID 1816352
Notes
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Reaction equation

HRID 1816352 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[S:30][C:29]([NH2:31])=[N:28][N:27]=4)=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Br[CH2:33][C:34]([C:36]1[CH:46]=[CH:45][C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][CH:37]=1)=O.C(OC(C)C)(C)C>C(O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([N:14]2[CH2:15][CH2:16][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[S:30][C:29]5=[N:31][C:34]([C:36]6[CH:46]=[CH:45][C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][CH:37]=6)=[CH:33][N:28]5[N:27]=4)=[CH:22][CH:21]=3)[CH2:18][CH2:19]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 11966043Ethyl 4-(2-bromoacetyl)benzoateHCID 22492898HCID 22492898, compound

Product 1

HCID 22492912HCID 22492912, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-[4-(1-cyclohexyl-4-piperidyl)phenyl]-1,3,4-thiadiazol-2-amine trifluoroacetate (0.78 g) and ethyl 4-(bromoacetyl)benzoate (0.6 g) in ethanol (15 ml) was stirred for 5 hours at 80° C. After being cooled to room temperature, the reaction mixture was poured into isopropyl ether. The resulting precipitate was collected by filtration, washed with isopropyl ether and added to a solution of trifluoroacetic acid (1.5 ml) in xylene (15 ml). Then a mixture was stirred for 3 hours at 130° C. After being cooled to room temperature, the reaction mixture was poured into isopropyl ether. The resulting precipitate was collected by filtration and washed with isopropyl ether to give ethyl 4-[2-[4-(1-cyclohexyl-4-piperidyl)phenyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoate trifluroacetate (0.45 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with isopropyl ether
  4. additionadded to a solution of trifluoroacetic acid (1.5 ml) in xylene (15 ml)
  5. stirringThen a mixture was stirred for 3 hours at 130° C
  6. temperatureAfter being cooled to room temperature
  7. additionthe reaction mixture was poured into isopropyl ether
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-95ce74ad59c943d3aa0c6eb056a6af4e
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884774B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes