Dimethylformamide → HCID 66725920, compound

HRID 1042099Notes

Reaction equation

HRID 1042099 reaction equation
[CH3:1][S:2]([C:5]1[CH:30]=[CH:29][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](O)=[O:27])=[CH:13]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.C[N:33](C)CCCN=C=NCC.[NH4+].ON1C2C=CC=CC=2N=N1.CN(C)C=O>CCCCCC.C(OCC)(=O)C.CO.O>[CH3:1][S:2]([C:5]1[CH:30]=[CH:29][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]([NH2:33])=[O:27])=[CH:13]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 667261715-[4-(Methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid

Product 1

HCID 66725920HCID 66725920, compoundYield 105.9%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid (1.95 g), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.73 g), 1-hydroxybenzotriazole ammonium salt (1.37 g), and N,N-dimethylformamide (50 mL) was stirred at room temperature for 12 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 silica gel column chromatography (methanol:ethyl acetate:hexane=0:85:15 to 10:90:0, volume ratio) to give the title compound (2.06 g, yield 100%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 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-f0175ad4732a45a589fa995bde7b8b1e
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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