Ammonia → HCID 66726191, compound

HRID 1042130Notes

Reaction equation

HRID 1042130 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21](O)=[O:22])=[CH:15]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.O[N:26]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N>O.CN(C)C=O>[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([NH2:26])=[O:22])=[CH:15]3)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66726156HCID 66726156, compound

Product 1

HCID 66726191HCID 66726191, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid (5.2 g), 1-hydroxybenzotriazole monohydrate (3.6 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.5 g) and N,N-dimethylformamide (200 mL) was stirred at 80° C. for 1 hr. The reaction mixture was cooled to room temperature and 10% aqueous ammonia (12 mL) was added, and the mixture was stirred at room temperature for 1 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 crystallized from diethyl ether to give the title compound (5.18 g, yield 100%) as pale-yellow powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crude product
  9. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-f97b8bc004a04c23a4b67948ce75c826
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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