Ammonium Hydroxide → HCID 58237070, compound

HRID 1189019Notes

Reaction equation

HRID 1189019 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][N:25]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:15][CH:16]([CH2:19][C:20](O)=[O:21])[CH2:17][N:18]=1)=[CH:10]2)[CH3:3].Cl.C([N:37]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[OH-].[NH4+]>O.CN(C)C=O>[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:26][N:25]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:15][CH:16]([CH2:19][C:20]([NH2:37])=[O:21])[CH2:17][N:18]=1)=[CH:10]2)[CH3:3]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58236984HCID 58236984, compound

Product 1

HCID 58237070HCID 58237070, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of {2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid (230 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 mg), 1-hydroxybenzotriazole (100 mg) and N,N-dimethylformamide (5 mL) was stirred at 50° C. for 30 min, and then cooled to 0° C. To the mixture was added aqueous ammonium hydroxide solution (10%, 1 mL). The whole was stirred at room temperature for 15 h. Water was added to the residue and the resultant was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10, volume ratio) to give pale yellow crystals. The crystals were recrystallized from acetone-hexane to give the title compound (90 mg, 39%) as pale yellow prisms. MS 489 (MH+). mp 212-213° C.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe whole was stirred at room temperature for 15 h
  3. extractionthe resultant was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10, volume ratio)
  9. customto give pale yellow crystals
  10. customThe crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-c046a040a6c944b6a77b598874f1898d
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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