Triethylamine → HCID 178462100, compound

HRID 1670527Notes

Reaction equation

HRID 1670527 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.Cl.[CH3:12][C@@H:13]([NH2:18])[C:14]([F:17])([F:16])[F:15].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.C(N(CC)CC)C>CN(C=O)C.O>[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][C@H:13]([CH3:12])[C:14]([F:17])([F:16])[F:15])=[O:8])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 44593757(2R)-1,1,1-Trifluoropropan-2-amine--hydrogen chloride (1/1)HCID 1785245186-sulfanylpyridine-3-carboxylic acid

Product 1

HCID 178462100HCID 178462100, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combine 6-mercapto-nicotinic acid (655 mg, 4.2 mmol), (R)-1-methyl-2,2,2-trifluoro-ethylamine hydrochloride (634 mg, 4.2 mmol) and EEDQ (1.06 g, 4.3 mmol) in anhydrous DMF (3 mL). Add triethylamine (0.6 mL, 4.3 mmol) and stir at room temperature for 16 h. Dilute the reaction mixture with water and extract with EtOAc (4×40 mL). Wash the combined organic extracts with brine, dry over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (3:2) to obtain the title compound as a yellow solid (180 mg, 18%). MS (ES+) m/z: 251.2 (M+H)+.

Workup

  1. extractionextract with EtOAc (4×40 mL)
  2. washWash the combined organic extracts with brine
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-99200e26fedb4c1e8436bec2b5bac7bb
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

Loading…