Water → HCID 178522810, compound

HRID 1670519Notes

Reaction equation

HRID 1670519 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.O>CN(C=O)C>[CH2:11]([NH:18][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([SH:1])=[N:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 1785245186-sulfanylpyridine-3-carboxylic acid

Product 1

HCID 178522810HCID 178522810, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 6-mercapto-nicotinic acid (0.64 g, 4.1 mmol), benzylamine (0.45 mL, 4.1 mmol) and EEDQ (1 g, 4 mmol) in anhydrous DMF (3 mL). Stir at room temperature for 12 h. Dilute the reaction with water and extract with DCM. Dry over MgSO4, filter and concentrate in vacuo to give a yellow solid. Purify by chromatography on silica gel eluting with 2M ammonia in methanol/DCM (2:98 and 10:90) to give the title compound as a yellow solid (440 mg, 44%). MS (ES+) m/z: 245 (M+H)+.

Workup

  1. additionDilute
  2. extractionextract with DCM
  3. dry with materialDry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customto give a yellow solid
  7. customPurify by chromatography on silica gel eluting with 2M ammonia in methanol/DCM (2:98 and 10:90)

Sources & evidence

ORD record
ord-b02f8c70926843ff903df8704e6b55cb
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

Loading…