Triethylamine → HCID 19699133, compound

HRID 863045Notes

Reaction equation

HRID 863045 reaction equation
[CH3:1][N:2]1[CH:11]=[C:10]2[C:4]([C:5]3[S:23][CH:22]=[CH:21][C:6]=3[N:7]([C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH2:8][CH2:9]2)=[N:3]1.C(N(CC)CC)C.[Cl:31][C:32]1[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:33]=1[C:34](Cl)=[O:35]>C(Cl)Cl.O1CCOCC1>[CH3:1][N:2]1[CH:11]=[C:10]2[C:4]([C:5]3[S:23][CH:22]=[CH:21][C:6]=3[N:7]([C:12]([C:13]3[CH:14]=[CH:15][C:16]([NH:19][C:34](=[O:35])[C:33]4[CH:37]=[CH:38][C:39]([Cl:41])=[CH:40][C:32]=4[Cl:31])=[CH:17][CH:18]=3)=[O:20])[CH2:8][CH2:9]2)=[N:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 19699068HCID 19699068, compound

Product 1

HCID 19699133HCID 19699133, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To an ice bath cooled mixture of 290 mg of 2,4,5,6-tetrahydro-2-methyl-6-(4-aminobenzoyl)pyrazolo[3,4-d]thieno[3,2-b]azepine in 4.0 ml of methylene chloride and 2.0 ml of dioxane under argon is added 186 μl of triethylamine followed by 156 μof 2,4-dichlorobenzoyl chloride. The reaction mixture is stirred at room temperature for 18 hours under argon. The reaction mixture is evaporated in vacuo to a residue which is dissolved in 50 ml of methylene chloride and washed with 20 ml each of water, 1N NaHCO3, 2N citric acid and brine. The organic layer is dried (Na2SO4) and filtered. The filtrate is concentrated in vacuo to give a foam residue which is crystallized from ethyl acetate to give 330 mg of the desired product as a white crystalline solid, m.p. 265°-267° C.

Workup

  1. temperatureTo an ice bath cooled
  2. customThe reaction mixture is evaporated in vacuo to a residue which
  3. dissolutionis dissolved in 50 ml of methylene chloride
  4. washwashed with 20 ml each of water, 1N NaHCO3, 2N citric acid and brine
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo
  8. customto give a foam residue which
  9. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-8b5a8416603349c0a26b94ed603e82da
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

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