Triethylamine → HCID 87121557, compound

HRID 599383Notes

Reaction equation

HRID 599383 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:70]2[CH:75]=[CH:74][C:73]([O:76][CH3:77])=[CH:72][CH:71]=2)([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[O:10][CH2:11][CH2:12][CH2:13][N:14]([C:46]2[CH:51]=[CH:50][C:49]([N:52]=[N:53][C:54]3[CH:59]=[CH:58][C:57]([N+:60]([O-:62])=[O:61])=[CH:56][C:55]=3[Cl:63])=[CH:48][CH:47]=2)[CH2:15][CH2:16][CH2:17][C:18]([N:20]2[C:31]3[C:23](=[C:24]4[C:28](=[CH:29][CH:30]=3)[NH:27][CH:26]([C:32](OC3C(F)=C(F)C(F)=C(F)C=3F)=[O:33])[CH2:25]4)[CH:22]=[CH:21]2)=[O:19])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:85]1[C:89]2=[C:90]3[C:94](=[CH:95][CH:96]=[C:88]2[NH:87][CH:86]=1)[NH:93][CH:92]([C:97]([N:99]1[C:110]2[C:102](=[C:103]4[C:107](=[CH:108][CH:109]=2)[NH:106][CH:105]([C:111]([O:113][CH2:114][CH2:115][C:116]2[CH:121]=[CH:120][C:119]([N+:122]([O-:124])=[O:123])=[CH:118][CH:117]=2)=[O:112])[CH2:104]4)[CH:101]=[CH:100]1)=[O:98])[CH2:91]3>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:70]2[CH:75]=[CH:74][C:73]([O:76][CH3:77])=[CH:72][CH:71]=2)([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[O:10][CH2:11][CH2:12][CH2:13][N:14]([C:46]2[CH:51]=[CH:50][C:49]([N:52]=[N:53][C:54]3[CH:59]=[CH:58][C:57]([N+:60]([O-:62])=[O:61])=[CH:56][C:55]=3[Cl:63])=[CH:48][CH:47]=2)[CH2:15][CH2:16][CH2:17][C:18]([N:20]2[C:31]3[C:23](=[C:24]4[C:28](=[CH:29][CH:30]=3)[NH:27][CH:26]([C:32]([N:87]3[C:88]5[C:89](=[C:90]6[C:94](=[CH:95][CH:96]=5)[NH:93][CH:92]([C:97]([N:99]5[C:110]7[C:102](=[C:103]8[C:107](=[CH:108][CH:109]=7)[NH:106][CH:105]([C:111]([O:113][CH2:114][CH2:115][C:116]7[CH:117]=[CH:118][C:119]([N+:122]([O-:124])=[O:123])=[CH:120][CH:121]=7)=[O:112])[CH2:104]8)[CH:101]=[CH:100]5)=[O:98])[CH2:91]6)[CH:85]=[CH:86]3)=[O:33])[CH2:25]4)[CH:22]=[CH:21]2)=[O:19])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 667169662-(4-Nitrophenyl)ethyl 3-(pyrrolo[4,5-e]indolin-7-ylcarbonyl)pyrrolo[4,5-e]indoline-7-carboxylateHCID 87121572HCID 87121572, compound

Product 1

HCID 87121557HCID 87121557, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 100 mL round bottom flask is weighed out 1.31 g (1.22 mmol) of 24. This is dissolved in 25 mL of dimethylformamide. Then 0.81 mL of triethylamine is added, and finally 0.623 g (1.162 mmol) of 17. The reaction mixture is left overnight, then the solution is concentrated to ˜10 mL and the resultant precipitate is filtered off, using a sintered glass filter funnel. The solid is washed with generous volumes of methanol (stirring the sludge in the filter with the methanol before applying the vacuum) several times and ether. When the effluent is clear and essentially colorless, the deep violet precipitate is dried in vacuo to afford 1.5 g (90%) of the desired product. 1H NMR (DMSO-d6) δ 11.96 (s, indole NH, 1H), 11.76 (s, indole NH, 1H), 11.69 (s, indole NH, 1H), 8.43 (d, J-2.4 Hz, aromatic proton, 1H), 8.35-8.20 (m, aromatic protons, 4H), 8.19 (d, J=9 Hz, aromatic protons, 2H), 7.85-7.75 (m, aromatic protons, 3H), 7.66 (d, J=9Hz, aromatic protons, 2H), 7.45-7.18 (m, aromatic protons, 12H), 7.10 (s, aromatic proton, 1H), 7.01 (s, aromatic proton, 1H), 6.99 (m, aromatic protons, 3H), 6.88 (d, J=9 Hz, aromatic protons, 4H), 4.61 (m, aliphatic protons, 6H), 4.14 (t, J=8.5 Hz, aliphatic protons, 2H), 3.71 (s, 2×CH3O, 6H), 3.59 (m, aliphatic protons, 2H), 3.43 (m, aliphatic protons, 6H), 3.34 (m, obscured by water signal, aliphatic protons, 2H), 3.22 (m, aliphatic protons, 2H), 3.08 (t, J=5 Hz, aliphatic protons, 2H), 2.5 (t, obscured by DMSO signal, COCH2—, 2H), 1.89 (br m, aliphatic protons, 4H).

Workup

  1. customInto a 100 mL round bottom flask is weighed out
  2. concentrationthe solution is concentrated to ˜10 mL
  3. filtrationthe resultant precipitate is filtered off
  4. filtrationfilter funnel
  5. washThe solid is washed with generous volumes of methanol (
  6. filtrationfilter with the methanol
  7. customessentially colorless, the deep violet precipitate is dried in vacuo

Sources & evidence

ORD record
ord-a5ee6770e1214d2183cc87ed3d18ef3f
Source dataset
uspto-grants-2011_03
Patent number
US07897736B2

Reaction notes

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