Dimethylformamide → HCID 67118513, compound

HRID 1188977Notes

Reaction equation

HRID 1188977 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][O:8][C:9]1[CH:10]=[C:11]([O:27][C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][CH:20]([CH2:23][C:24]([OH:26])=O)[CH2:21][N:22]=1)=[CH:14]2.Cl.C[N:40](C)CCCN=C=NCC.[NH4+].ON1C2C=CC=CC=2N=N1.CN(C)C=O>C(OCC)(=O)C.CO>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][O:8][C:9]1[CH:10]=[C:11]([O:27][C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:35])=[O:36])=[CH:30][CH:29]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][CH:20]([CH2:23][C:24]([NH2:40])=[O:26])[CH2:21][N:22]=1)=[CH:14]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 67118499HCID 67118499, compound

Product 1

HCID 67118513HCID 67118513, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-{7-[(1-methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (210 mg), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (150 mg), 1-hydroxybenzotriazole ammonium salt (118 mg) and N,N-dimethylformamide was stirred at room temperature for 5 hr. The reaction solution was concentrated under reduced pressure, water was added to the residue, and the mixture was washed with diisopropyl ether. Sodium chloride was added to the aqueous layer to give a saturated solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (methanol:ethyl acetate=0:100 to 25:75, volume ratio), and the obtained amorphous solid was crystallized from diethyl ether to give the title compound (50 mg, yield 24%) as colorless crystals. melting point 130-131° C. MS 540 (MH+).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. washthe mixture was washed with diisopropyl ether
  4. additionSodium chloride was added to the aqueous layer
  5. customto give a saturated solution
  6. extractionthe mixture was subjected to extraction with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained crude product
  11. customthe obtained amorphous solid was crystallized from diethyl ether

Sources & evidence

ORD record
ord-205d543441704c11a6af933777fdbb90
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…