Triethylamine → HCID 86613660, compound

HRID 2193487Notes

Reaction equation

HRID 2193487 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH:13]1[CH:8]([CH2:9][CH2:10][CH:11]([O:19][C:20](=[O:22])[CH3:21])[CH2:12]1)[N:7]=[C:6]2[C:23]1[CH:28]=[CH:27][C:26]([C:29]([NH:31][C:32](=[NH:35])SC)=[O:30])=[CH:25][CH:24]=1.[C:36]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)(=[O:38])[CH3:37].C(N(CC)CC)C>O1CCOCC1>[C:36]([N:39]1[CH2:44][CH2:43][N:42]([C:32](=[N:31][C:29]([C:26]2[CH:27]=[CH:28][C:23]([C:6]3[C:5]4[C:14](=[CH:15][C:16]([O:17][CH3:18])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:13]4[CH:8]([CH2:9][CH2:10][CH:11]([O:19][C:20](=[O:22])[CH3:21])[CH2:12]4)[N:7]=3)=[CH:24][CH:25]=2)=[O:30])[NH2:35])[CH2:41][CH2:40]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 837951-Acetylpiperazine2×HCID 140517263HCID 140517263, compound2×

Product 1

HCID 86613660HCID 86613660, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

743.4 mg of acetic acid (2RS,4aRS,10bRS)-8,9-dimethoxy-6-{4-[1-(2-methyl-isothioureido)-methanoyl]-phenyl}-1,2,3,4,4a,10b-hexahydro-phenanthridin-2-yl ester (compound A1), 384.5 mg of 1-acetylpiperzine and 0.416 ml of triethylamine are stirred in 10 ml of 1,4-dioxane at 90° C. for 5 days. After 2 days another 384.5 mg of 1-acetylpiperazine are added to the reaction mixture. The solvent is removed and the residue three times coevaporated with dichloromethane, than one time with toluene. After redissolving in 25 ml of dichloromethane the solution is extracted with water and aqueous saturated KHCO3 solution successively and the aqueous KHCO3 phase reextracted with dichloromethane. After drying the combined organic layers with sodium sulfate the solvent is removed and the residue purified by chromatography on silica to yield 530 mg of the title compound.

Workup

  1. customThe solvent is removed
  2. dissolutionAfter redissolving in 25 ml of dichloromethane the solution
  3. extractionis extracted with water and aqueous saturated KHCO3 solution successively
  4. dry with materialAfter drying the combined organic layers with sodium sulfate the solvent
  5. customis removed
  6. customthe residue purified by chromatography on silica

Sources & evidence

ORD record
ord-40d54df9e2c64332a25f3ae7f917a364
Source dataset
uspto-grants-2012_12
Patent number
US08329906B2

Reaction notes

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