Ammonia → HCID 66726152, compound

HRID 1042119Notes

Reaction equation

HRID 1042119 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[N:11]=[CH:10][C:9]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[C:20]([O:22][CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH:21]=2)[NH:18][C:17]([C:29]([OH:31])=O)=[CH:16]3)=[CH:8][CH:7]=1)(=[O:4])=[O:3].O.O[N:34]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N>CN(C)C=O.CCCCCC.C(OCC)(=O)C.O>[CH3:1][S:2]([CH2:5][C:6]1[N:11]=[CH:10][C:9]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[C:20]([O:22][CH:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[CH:21]=2)[NH:18][C:17]([C:29]([NH2:34])=[O:31])=[CH:16]3)=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

9

Reactant 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66725942HCID 66725942, compound

Product 1

HCID 66726152HCID 66726152, compoundYield 61.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-{[6-(methylsulfonylmethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid (4.9 g) in N,N-dimethylformamide (20 mL) were added 1-hydroxybenzotriazole monohydrate (2.68 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.3 g), and 25% aqueous ammonia (15 mL), and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=0:100 to 100:0, volume ratio) to give the title compound (3.0 g, yield 58%) as pale-yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude product

Sources & evidence

ORD record
ord-e91bb44a431740c29b77af3401e372aa
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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