Triethylamine → HCID 86613660, compound

HRID 731681Notes

Reaction equation

HRID 731681 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-a1e90ccea94049b7bf17be5eecdd7f8a
Source dataset
uspto-grants-2009_09
Patent number
US07585872B2

Reaction notes

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