Oxamic Acid → HCID 16039524, compound

HRID 1984011Notes

Reaction equation

HRID 1984011 reaction equation
[C:1](O)(=[O:5])[C:2]([NH2:4])=[O:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:21]([CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][N:33]([C:36]3[CH:37]=[C:38]4[C:42](=[CH:43][CH:44]=3)[NH:41][CH:40]=[CH:39]4)[CH2:32][CH2:31]2)[CH2:20]1>CN(C)C=O>[NH:41]1[C:42]2[C:38](=[CH:37][C:36]([N:33]3[CH2:32][CH2:31][N:30]([CH2:29][CH2:28][C@H:21]4[C:22]5[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:19]([C:1](=[O:5])[C:2]([NH2:4])=[O:3])[CH2:20]4)[CH2:35][CH2:34]3)=[CH:44][CH:43]=2)[CH:39]=[CH:40]1

Participants

5

Reactant 3

HCID 974Oxamic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 68854443HCID 68854443, compound

Product 1

HCID 16039524HCID 16039524, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of oxalamic acid (2.35 g, 0.026 mol) and 1,1′-carbonyldiimidazole (4.66 g, 0.029 mol) in dry N,N-dimethyl formamide (50 mL) was slowly added a solution of 5-{4-[(S)-2-(2,3-dihydro-1H-indol-3-yl)-ethyl]-piperazin-1-yl}-1H-indole (8.3 g, 0.024 mol) in N,N-dimethyl formamide (75 mL). The resulting mixture was stirred at room temperature for 1 h, filtered and poured onto brine. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/heptane/triethylamine 70:25:5) to give the title compound as an oil (6.5 g). The oil was precipitated from ethyl acetate to give a powder (4.1 g). Assignment of the optical rotation was done in dimethyl sulfoxide.

Workup

  1. filtrationfiltered
  2. additionpoured onto brine
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (ethyl acetate/heptane/triethylamine 70:25:5)

Sources & evidence

ORD record
ord-a999557fc4094928aef42746d3e5397c
Source dataset
uspto-grants-2009_06
Patent number
US07544685B2

Reaction notes

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