Triethylamine → HCID 21940019, compound

HRID 1242945Notes

Reaction equation

HRID 1242945 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([NH2:15])[CH:9]=[CH:8][C:7]=2[CH:6]=1)[CH3:3].C(N(CC)CC)C.[C:23]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[CH:27][C:26]([S:29]([Cl:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(#N)C>[ClH:32].[CH3:3][N:2]([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([NH:15][S:29]([C:26]3[CH:25]=[CH:24][C:23]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:28][CH:27]=3)(=[O:31])=[O:30])[CH:9]=[CH:8][C:7]=2[CH2:6]1)[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 21939779HCID 21939779, compound

Product 1

HCID 21940019HCID 21940019, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-[(N,N-Dimethylamino)methyl]-7,8-dihydro-2-naphthalenamine (200 mg, 0.72 mmol) obtained in Example 41-2) was dissolved in acetonitrile (30 ml). Triethylamine (0.401 ml, 2.88 mmol) and [1,1′-biphenyl]-4-sulfonylchloride (200 mg, 0.79 mmol) were added to the solution under ice-cooling, which was stirred for 3 hours. The reaction mixture was concentrated. Ethyl acetate and water were added to the residue, and extraction was conducted. The ethyl acetate layer was concentrated, and the residue was purified by alumina column chromatography (development solvent; ethyl acetate: n-hexane=33:67). 4N Hydrogen chloride-ethyl acetate solution was added to the resulting oily substance, which was concentrated. The residue was recrystallized from methanol-ethyl acetate, to give the titled compound (194 mg).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionEthyl acetate and water were added to the residue, and extraction
  4. concentrationThe ethyl acetate layer was concentrated
  5. customthe residue was purified by alumina column chromatography (development solvent; ethyl acetate: n-hexane=33:67)
  6. addition4N Hydrogen chloride-ethyl acetate solution was added to the resulting oily substance, which
  7. concentrationwas concentrated
  8. customThe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-cabec7ab783c4e05910f1ccb51d70e5d
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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