Triethylamine → HCID 10024664, compound

HRID 392160Notes

Reaction equation

HRID 392160 reaction equation
[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][C@@H:2]1[CH2:15]OS(C1C=CC(Br)=CC=1)(=O)=O)[N:11]=[CH:10][CH:9]=[CH:8]3.[C:27]([C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH:33]=[C:32]2[CH2:38][CH2:39][CH2:40][NH2:41])#[N:28].[CH2:42](N(CC)CC)C>CS(C)=O>[CH3:42][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][CH:14]=[C:5]3[O:4][CH2:3][CH:2]([CH2:15][NH:41][CH2:40][CH2:39][CH2:38][C:32]4[C:31]5[C:35](=[CH:36][CH:37]=[C:29]([C:27]#[N:28])[CH:30]=5)[NH:34][CH:33]=4)[O:1][C:6]3=2)[N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3886025HCID 3886025, compoundHCID 87799086HCID 87799086, compound

Product 1

HCID 10024664HCID 10024664, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (2R)-4-bromobenzenesulfonic acid 2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl ester (1.13 g, 2.5 mmol), 3-(5-cyano-1H-indol-3-yl)propylamine (0.65 g, 3.2 mmol) and triethylamine (0.7 mL, 5.0 mmol) in dimethylsulfoxide (40 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 0.54 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, m.p. 170-174° 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-efaaa526e66d45b7b6fdd0d57993b864
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Reaction notes

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