Triethylamine → 8-{{3-[(5-METHOXY-DIHYDRO-[2H]-BENZO[b]PYRAN-3-YL)AMINO]PROPYL}OXY}THIOCHROMAN

HRID 1491807Notes

Reaction equation

HRID 1491807 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[S:14][CH2:13][CH2:12][CH2:11]2.[NH2:16][CH:17]1[CH2:22][O:21][C:20]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:19]=2[CH2:18]1.C(N(CC)CC)C>CN(C)C=O>[CH3:28][O:27][C:26]1[C:19]2[CH2:18][CH:17]([NH:16][CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:15]=3[S:14][CH2:13][CH2:12][CH2:11]4)[CH2:22][O:21][C:20]=2[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139289485-Methoxy-3,4-dihydro-2H-1-benzopyran-3-amineHCID 152958308-[(3-Bromopropyl)oxy]thiochroman

Product 1

HCID 30739328-{{3-[(5-METHOXY-DIHYDRO-[2H]-BENZO[b]PYRAN-3-YL)AMINO]PROPYL}OXY}THIOCHROMAN

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 1.6 g (5.58 mmol) of 8-[(3-bromopropyl) oxy]thiochroman, 1 g (5.58 mmol) of 3-amino-5-methoxy-dihydro-[2H]-benzo[b]pyran and 1.69 g (16.74 mmol) of triethylamine are dissolved in 20 cm3 of dimethylformamide. The mixture is kept at room temperature for 24 hours. The solvent is evaporated off. The residue is taken up in H2O and extracted with methylene chloride. The product is dried over MgSO4. After evaporation, the product is purified over a flash silica column. Eluant: methanol/CH2Cl2 5:95. The title compound is obtained (yellow oil).

Workup

  1. customThe solvent is evaporated off
  2. extractionextracted with methylene chloride
  3. dry with materialThe product is dried over MgSO4
  4. customAfter evaporation
  5. customthe product is purified over a flash silica column

Sources & evidence

ORD record
ord-99f8d3cf3233405291e593a523b9f0d2
Source dataset
uspto-grants-1994_12
Patent number
US05371103

Reaction notes

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