Triethylamine → HCID 53649915, compound

HRID 1954819Notes

Reaction equation

HRID 1954819 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)(=[O:4])=[O:3].[NH2:15][C@@H:16]1[CH2:25][CH2:24][C:23]2[C:18](=[C:19]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[CH:20]=[CH:21][CH:22]=2)[CH2:17]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:32][N:29]1[CH2:30][CH2:31][N:26]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[CH2:17][C@H:16]([NH:15][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][CH:14]=[C:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:7]=2)[CH2:25][CH2:24]3)[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 184757433-[(Methylsulfonyl)oxy]benzoic acidHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 53649915HCID 53649915, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 3-methanesulfonyloxybenzoic acid (0.20 g, 0.90 mmol; described in: Looker, J. H.; Hayes, C. H.; Thatcher, D. N. J. Am. Chem. Soc. 1957, 79, 741-4) in thionyl chloride (5 mL) was heated at 40° C. for 45 min (the solution became homogeneous). 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, 0.50 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, 0.48 mmol) and triethylamine (100 μL, 0.72 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 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 (100:4) as the eluent. Yield: 87 mg (41%) of the title compound as white crystals: mp 159-160° C.; [α]21D -27° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 443 (21, 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
  5. washwas then washed with dilute aqueous sodium hydrogen carbonate
  6. customThe phases were separated
  7. dry with materialthe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3358fbb3b0a94f518846baf3fbc42fe0
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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