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Diisopropyl Ether → HCID 22492950, compound

HRID 1816327
Notes
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Reaction equation

HRID 1816327 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][N:22]([CH:25]5[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]5)[CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[CH:32]([O:34][CH2:35][CH3:36])=[O:33].C(O)C.[O-]CC.[Na+].C(OC(C)C)(C)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:31][CH:28]1[CH2:29][CH2:30][CH:25]([N:22]2[CH2:23][CH2:24][N:19]([C:16]3[CH:17]=[CH:18][C:13]([C:11]4[S:12][C:8]([C:5]5[CH:6]=[CH:7][C:2]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:3][CH:4]=5)=[N:9][N:10]=4)=[CH:14][CH:15]=3)[CH2:20][CH2:21]2)[CH2:26][CH2:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8025Ethyl formateHCID 22492909HCID 22492909, compoundHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 22492950HCID 22492950, compound

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-[4-[5-(4-iodophenyl)-1,3,4-thiadiazol-2-yl]phenyl]-4-(4-methylcyclohexyl)piperazine (2 g) in DMF (40 ml) was successively added ethyl formate (0.56 ml), dichlorobis(triphenylphosphine)palladium(II) (0.52 g) and 20% sodium ethoxide ethanol solution (4.43 ml) with stirring and the mixture was stirred at 40° C. for 2 hours. The reaction mixture was added diisopropyl ether (600 ml). The resulting precipitate was collected by filtration. The precipitate was dissolved THF (200 ml), insoluble materials were filtered off and solution was concentrated in vacuo. The resulting residue was washed with acetonitrile, and dried to give ethyl 4-[5-[4-[4-(4-methylcyclohexyl)-1-piperazinyl]phenyl]-1,3,4-thiadiazol-2-yl]benzoate (1.07 g).

Workup

  1. stirringthe mixture was stirred at 40° C. for 2 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved THF (200 ml), insoluble materials
  4. filtrationwere filtered off
  5. concentrationsolution was concentrated in vacuo
  6. washThe resulting residue was washed with acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-ab64febad9a54cee84fea87e5c031566
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884774B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes