Triethylamine → HCID 17796542, compound

HRID 379566Notes

Reaction equation

HRID 379566 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.OC[CH:24]1[CH2:29][N:28](S(C2C=CC3C(=CC=C(Br)C=3)C=2)(=O)=O)[CH2:27][CH2:26][NH:25]1.C(N(CC)CC)C>ClCCl.O.CN(C=O)C>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH2:24]3)=[O:13])=[CH:14][CH:15]=2)=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chloride2×HCID 15208114-(Pyridin-4-yl)benzoic acidHCID 22329739HCID 22329739, compound

Product 1

HCID 17796542HCID 17796542, compoundYield 119.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 4-(4-pyridyl)benzoic acid (sodium salt) (190 mg, 0.86 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (0.2 ml, 2.3 mmol) and DMF (catalytic amount). After stirring for 2 hours, further oxalyl chloride 0.2 ml, 2.3 mmol) and DMF (catalytic amount) was added and the suspension stirred a further 4 hours. The solvent was removed in vacuo and the residue, after drying, was suspended in dichloromethane (20 ml) and treated with 2-(hydroxymethyl)-4-(6-bromonaphth-2-ylsulphonyl)piperazine (300 mg, 0.78 mmol) and triethylamine (0.36 ml, 2.5 mmol). After stirring at room temperature overnight the reaction mixture was diluted with dichloromethare (20 ml) and water (20 ml). A copious precipitate appeared which was filtered off, dried and recrystallised from ethyl acetate (10 ml) to yield 1-(6-bromonaphth-2-ylsulphonyl)-3hydroxymethyl)-4-[4-(4-pyridyl)benzoyl]piperazine as a colourless solid (250 mg); 1H NMR (300 MHz, DMSO-d6) δ=3-4 ppm (broad, 9H), δ=7.2 ppm (d, 2H), δ=7.7 ppm (d, 2H), δ=7.8 ppm (m, 4H), δ=8.2 ppm (t, 2H), δ=8.4 ppm (s, 1H), δ=8.45 ppm (s, 1H), δ=8.6 ppm (d, 2H); signals due to ethyl acetate (1 mol eq) were also present; MS: (M+H)+ 566/568 (1 Br pattern); analysis; found: C, 56.8; H, 4.9; N, 6.3%; C27H24BrN3SO4.C4H8O2 requires: C, 56.9; H, 4.9; N, 6.4%.

Workup

  1. stirringthe suspension stirred a further 4 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue, after drying
  4. stirringAfter stirring at room temperature overnight the reaction mixture
  5. filtrationwas filtered off
  6. customdried
  7. customrecrystallised from ethyl acetate (10 ml)

Sources & evidence

ORD record
ord-5e10e23cd6d540a386c34167b2d0bd6d
Source dataset
uspto-grants-2001_10
Patent number
US06300330B1

Reaction notes

Loading…