HCID 11323174, compound → HCID 54497369, compound

HRID 2187422Notes

Reaction equation

HRID 2187422 reaction equation
[F:1][C:2]([F:17])([F:16])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[NH2:18][C@@H:19]1[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)[CH:23]=[CH:24][CH:25]=2)[CH2:20]1>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:35][N:32]1[CH2:33][CH2:34][N:29]([C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:21]=2[CH2:20][C@H:19]([NH:18][C:13](=[O:15])[C:10]2[CH:9]=[CH:8][C:7]([O:6][S:3]([C:2]([F:1])([F:17])[F:16])(=[O:4])=[O:5])=[CH:12][CH:11]=2)[CH2:28][CH2:27]3)[CH2:30][CH2:31]1

Participants

5

Reactant 2

HCID 11323174HCID 11323174, compoundHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54497369HCID 54497369, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
40 °C

Procedure

4-Carboxyphenyl trifluoromethanesulfonate (0.40 g, 1.5 mmol; described in: Looker, J. H.; Hayes, C. H.; Thatcher, D. N. J. Am. Chem. Soc. 1957, 79, 741-4) was dissolved in thionyl chloride (10 mL) and heated at 40° C. for 45 min. The excess of thionyl chloride was evaporated in vacuo, the residue was treated with toluene and again the solvent was removed in vacuo. The crude acid chloride (280 mg, 0.96 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 (110 mg, 0.46 mmol) and triethylarine (96 μL, 0.69 mmol) in methylene chloride (20 mL). After the addition the reaction was allowed to stir at ambient temperature for 15 min and then washed with water. The phases were separated and the combined organic phases were 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: 100 mg (44%) of the title compound as white crystals: mp 178-180° C.; [α]21D −31° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 497 (17, M+).

Workup

  1. customThe excess of thionyl chloride was evaporated in vacuo
  2. additionthe residue was treated with toluene
  3. customagain the solvent was removed in vacuo
  4. additionAfter the addition the reaction
  5. washwashed with water
  6. customThe phases were separated
  7. dry with materialthe combined organic phases were dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d6916291e19745889e73c92b421f12d9
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

Loading…