Ammonia → HCID 66726292, compound

HRID 1042147Notes

Reaction equation

HRID 1042147 reaction equation
[CH3:1][S:2]([C:5]1[CH:36]=[CH:35][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([O:19][CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:18]=2)[NH:15][C:14]([C:26]2[S:27][CH:28]([CH2:31][C:32]([OH:34])=O)[CH2:29][N:30]=2)=[CH:13]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.C[N:39](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.N>CCCCCC.C(OCC)(=O)C.CO.O.CN(C)C=O>[CH3:1][S:2]([C:5]1[CH:36]=[CH:35][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([O:19][CH:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:18]=2)[NH:15][C:14]([C:26]2[S:27][CH:28]([CH2:31][C:32]([NH2:39])=[O:34])[CH2:29][N:30]=2)=[CH:13]3)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

10

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66726076HCID 66726076, compound

Product 1

HCID 66726292HCID 66726292, compoundYield 54.2%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (2-{5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (370 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (268 mg), 1-hydroxybenzotriazole (189 mg), and N,N-dimethylformamide (20 mL) was stirred at 50° C. for 30 min. The reaction solution was cooled to room temperature, 10% aqueous ammonia solution (1.0 mL) was added, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (methanol:ethyl acetate:hexane=0:50:50 to 10:90:0, volume ratio) to give the title compound (200 mg, yield 54%) as a white amorphous solid. The white amorphous solid was crystallized from diethyl ether and the obtained crystals were recrystallized from ethyl acetate-diethyl ether to give the title compound as colorless crystals.

Workup

  1. temperatureThe reaction solution 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 brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crude product

Sources & evidence

ORD record
ord-25672b6d27504c8d8248436e37601fce
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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