Triethylamine → HCID 10048117, compound

HRID 392163Notes

Reaction equation

HRID 392163 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14][C@H:13]([CH2:16]OS(C4C=CC(Br)=CC=4)(=O)=O)[O:12][C:8]3=2)[N:3]=1.[C:28]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([CH3:39])[CH:34]=[C:33]2[CH2:40][CH2:41][CH2:42][NH2:43])#[N:29].C(N(CC)CC)C>CS(C)=O>[CH3:39][N:35]1[C:36]2[C:32](=[CH:31][C:30]([C:28]#[N:29])=[CH:38][CH:37]=2)[C:33]([CH2:40][CH2:41][CH2:42][NH:43][CH2:16][CH:13]2[O:12][C:8]3=[C:9]4[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14]2)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]4)=[CH:34]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonateHCID 22662948HCID 22662948, compound

Product 1

HCID 10048117HCID 10048117, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (2R)-4-bromobenzenesulfonic acid-8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl ester (0.5 g, 1.1 mmol), 3-(5-cyano-1-methyl-indol-3-yl)propylamine (0.33 g, 1,4 mmol) and triethylamine (0.23 mL, 2.2 mmol) in dimethylsulfoxide (20 mL) was heated at 90° C. under nitrogen for 16 hours. The reaction mixture was quenched with 1N sodium hydroxide and extracted with methylene chloride (3×100 mL). The organic layer was washed with water (3×150 mL), dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum. The crude oil was column chromatographed on silica gel (10% methanol-ethyl acetate). The product-containing fractions were concentrated in vacuum to give 0.2 g of the (S)-enantiomer of the title compound as a brown oil. The dihydrochloride salt was prepared in ethyl acetate as a yellow solid (decomposed at 148° C.).

Workup

  1. customThe reaction mixture was quenched with 1N sodium hydroxide
  2. extractionextracted with methylene chloride (3×100 mL)
  3. washThe organic layer was washed with water (3×150 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under vacuum
  7. customchromatographed on silica gel (10% methanol-ethyl acetate)
  8. concentrationThe product-containing fractions were concentrated in vacuum

Sources & evidence

ORD record
ord-f67b57eb62684105b8cd26e11a38205f
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Reaction notes

Loading…