Triethylamine → HCID 9824760, compound

HRID 1954808Notes

Reaction equation

HRID 1954808 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)=[O:4].[NH2:16][C@@H:17]1[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)[CH:21]=[CH:22][CH:23]=2)[CH2:18]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:33][N:30]1[CH2:31][CH2:32][N:27]([C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:19]=2[CH2:18][C@H:17]([NH:16][C:9](=[O:11])[C:8]2[CH:7]=[CH:6][C:5]([C:3](=[O:4])[C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=2)[CH2:26][CH2:25]3)[CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1435794-(Trifluoroacetyl)benzoic acidHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 9824760HCID 9824760, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

4-(Trifluoroacetyl)benzoic acid (0.50 g, 2.4 mmol) was dissolved in thionyl chloride (15 mL) and heated at reflux for 20 min. 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 (97 mg, 0.43 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 (100 mg, 0.41 mmol) and triethylamine (85 μL, 0.61 mmol) in methylene chloride (35 mL). After the addition, the reaction was allowed to stir at ambient temperature for 15 min and was then washed with dilute aqueous sodium hydrogen carbonate. 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/ethanol saturated with NH3 (100:3) as the eluent. Yield: 98 mg (54%) of the title compound as slightly yellow crystals: mp 91-93° C.; [α]21D -47° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 453 (27, M+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 min
  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
  7. washwas then washed with dilute aqueous sodium hydrogen carbonate
  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-8ffacdd1039e48b19246e43b7677bf5c
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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