Water → HCID 59424233, compound

HRID 1172854Notes

Reaction equation

HRID 1172854 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15]([OH:17])=O)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].C[CH2:19][N:20]=C=NCCCN(C)C.[CH3:29]CN(CC)CC.[OH2:36]>CN(C=O)C>[CH3:29][O:36][N:20]([CH3:19])[C:15]([C:13]1[CH:12]=[CH:11][C:9]2[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][C:8]=2[CH:14]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 57443971HCID 57443971, compound

Product 1

HCID 59424233HCID 59424233, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-(ethoxycarbonyl)-1-benzothiophene-6-carboxylic acid (2.5 g, 10.0 mmol) was dissolved in DMF (20 mL) and cooled to 0° C. EDCI (1.92 g, 10.0 mmol) was added to the reaction followed by (MeO)NHMe.HCl (1.5 g, 15.0 mmol) and then Et3N (1.4 mL, 10.0 μmmol). The reaction was allowed to stir for 1 h at 0° C. Water was added to reaction mixture and then extracted with Et2O (3×). The combined organic layers were dried over Na2SO4, filtered, concentrated yielded the crude amide. Purification by flash column chromatography provided the desired amide. 1H NMR (CDCl3, 600 MHz) δ 8.20 (s, 1H), 8.04 (s, 1H), 7.87 (d, J=8.4 Hz, 1H), 7.69 (dd, J=8.4, 1.0 Hz, 1H), 4.39 (d, J=7.2 Hz, 2H), 3.54 (s, 3H), 3.38 (s, 3H), 1.4 (t, J=7.2 Hz, 3H). MS: cal'd (MH+) 294, exp (MH+) 294.

Workup

  1. extractionextracted with Et2O (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customyielded the crude amide
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-f17d6e3d9f0c442da4b69b4b2b229a4b
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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