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Sodium Carbonate → HCID 10120773, compound

HRID 1989855
Notes
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Reaction equation

HRID 1989855 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].Br[CH:39]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:40]([O:42][CH3:43])=[O:41]>CN(C=O)C>[C:44]1([CH:39]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[CH:9][C:10]([NH:13][C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][CH:23]=4)=[O:15])=[CH:11][CH:12]=3)[CH2:2][CH2:3]2)[C:40]([O:42][CH3:43])=[O:41])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 112010994'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(piperazinyl)-phenyl]-amide

Product 1

HCID 10120773HCID 10120773, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of intermediate (2) (0.007 mol) and Na2CO3 (0.007 mol) in DMF (50 ml) was stirred. Methyl 2-bromo-2-phenylacetate (0.007 mol) was added dropwise. The mixture was stirred for 4 hours. The solvent was evaporated. The residue was dissolved in DCM. The organic layer was separated, washed, dried, filtered and the solvent was evaporated. The residue was triturated in 2-propanol. The precipitate was filtered off and dried, yielding 3.34 g of methyl α-phenyl-4-[4-[[[4′-(trifluoromethyl)[1,1′-biphenyl]-2-yl]carbonyl]amino]phenyl]-1-piperazineacetate (intermediate 3).

Workup

  1. stirringThe mixture was stirred for 4 hours
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. customThe organic layer was separated
  5. washwashed
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was triturated in 2-propanol
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-72da7684fd0847ed92a072950fe64e2e
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07642378B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes