Triethylamine → HCID 54512534, compound

HRID 2187449Notes

Reaction equation

HRID 2187449 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:17][C@@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[C:21]([N:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[CH:22]=[CH:23][CH:24]=2)[CH2:19]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:34][N:31]1[CH2:32][CH2:33][N:28]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:20]=2[CH2:19][C@H:18]([NH:17][C:14](=[O:16])[C:11]2[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=4)=[CH:13][CH:12]=2)[CH2:27][CH2:26]3)[CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54512534HCID 54512534, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

4′-Hydroxy-4-biphenylcarboxylic acid (0.40 g, 1.9 mmol) was dissolved in thionyl chloride (10 mL) and heated at reflux for 1 h. The excess of thionyl chloride was evaporated in vacuo, the residue was treated with toluene and again the solvent was removed in vacuo. Crude acid chloride (120 mg, 0.51 mmol) was dissolved in methylene chloride (5 mL) and added dropwise to an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.49 mmol) and triethylamine (100 μL, 0.74 mmol) in methylene chloride (20 mL) . After the addition the reaction was allowed to stir at ambient temperature for 15 min and was then washed with water. The phases were separated and the organic phase was dried (Na2SO4), filtered and evaporated in vacuo to give a crude product which was purified on a silica gel column using chloroform/methanol/concentrated ammonium hydroxide (95:6:0.5) as the eluent. Yield: 95 mg (44%) of the title compound as white crystals: mp 261-262° C.; EIMS (70 eV) m/z (relative intensity) 441 (2, M+)

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customThe excess of thionyl chloride was evaporated in vacuo
  4. additionthe residue was treated with toluene
  5. customagain the solvent was removed in vacuo
  6. additionAfter the addition the reaction
  7. washwas then washed with water
  8. customThe phases were separated
  9. dry with materialthe organic phase was dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-244b0c30ac7d45a4ab5280ac609d5b1b
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

Loading…