Maleic Acid → HCID 68525872, compound

HRID 884192Notes

Reaction equation

HRID 884192 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2C=CC(CNCC(O)=O)=[CH:17][CH:16]=2)=[N:12][CH:13]=1)=[O:6].[O:31]1[C:36]2[CH:37]=[CH:38][C:39]([CH2:41][N:42]3[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)=[CH:40][C:35]=2[O:34][CH2:33][CH2:32]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N[CH2:65][CH2:66][CH2:67][N:68]([CH3:70])[CH3:69])C.[C:71]([OH:78])(=[O:77])/[CH:72]=[CH:73]\[C:74]([OH:76])=[O:75]>CN(C=O)C>[C:71]([OH:78])(=[O:77])/[CH:72]=[CH:73]\[C:74]([OH:76])=[O:75].[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1[CH:13]=[N:12][C:11]([O:14][C:15]2[CH:65]=[CH:66][C:67]([N:68]([CH2:69][C:74]([N:45]3[CH2:46][CH2:47][N:42]([CH2:41][C:39]4[CH:38]=[CH:37][C:36]5[O:31][CH2:32][CH2:33][O:34][C:35]=5[CH:40]=4)[CH2:43][CH2:44]3)=[O:75])[CH3:70])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

7

Reactant 5

HCID 444266Maleic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 49622611-[(2,3-Dihydro-1,4-benzodioxin-6-yl)methyl]piperazineHCID 68525947HCID 68525947, compound

Product 1

HCID 68525872HCID 68525872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ({4-[5-(3,4-dichlorobenzoyl-amino)pyridin-2-yloxy]phenyl}methylamino)acetic acid (2.50 g, 5.6 mmol) in DMF (55 mL) were added 1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)piperazine (1.7 g, 7.3 mmol), 1-hydroxybenzotriazole monohydrate (0.86 g, 5.6 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.29 g, 6.7 mmol) under ice cooling, and the resulting solution was stirred for 30 minutes under ice cooling and for 17 hours at room temperature. This reaction solution was concentrated under reduced pressure. Water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was dissolved in ethanol (30 mL). To the resulting solution was added maleic acid (0.32 g, 2.7 mmol), and this solution was left to stand. The precipitates were collected by filtration, to thereby yield 1.45 g of the title compound.

Workup

  1. concentrationThis reaction solution was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue was dissolved in ethanol (30 mL)
  8. waitthis solution was left
  9. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-b2b2be48ffa04c9683e4f2bd5ef47133
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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