Piperidine → HCID 86717256, compound

HRID 1482766Notes

Reaction equation

HRID 1482766 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[C:10]([O:60][CH2:61][CH2:62][CH2:63][O:64][C:65]2[C:92]([O:93][CH3:94])=[CH:91][C:68]3[C:69](=[O:90])[N:70]4[CH:76]=[C:75]([C:77]5[CH:82]=[CH:81][C:80]([N:83]6[CH2:88][CH2:87][N:86]([CH3:89])[CH2:85][CH2:84]6)=[CH:79][CH:78]=5)[CH2:74][C@H:71]4[CH:72]=[N:73][C:67]=3[CH:66]=2)=[CH:11][C:12]2[N:18]=[CH:17][C@@H:16]3[CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:57])[C@@H:30]([NH:32][C:33](=[O:56])[C@@H:34]([NH:38]C(=O)OCC5C6C=CC=CC=6C6C5=CC=CC=6)[CH:35]([CH3:37])[CH3:36])[CH3:31])=[CH:24][CH:23]=4)=[CH:21][N:15]3[C:14](=[O:58])[C:13]=2[CH:59]=1>CN(C=O)C.C(Cl)Cl>[NH2:38][C@@H:34]([CH:35]([CH3:37])[CH3:36])[C:33]([NH:32][C@@H:30]([CH3:31])[C:29]([NH:28][C:25]1[CH:24]=[CH:23][C:22]([C:20]2[CH2:19][C@H:16]3[N:15]([CH:21]=2)[C:14](=[O:58])[C:13]2[CH:59]=[C:9]([O:8][CH3:7])[C:10]([O:60][CH2:61][CH2:62][CH2:63][O:64][C:65]4[C:92]([O:93][CH3:94])=[CH:91][C:68]5[C:69](=[O:90])[N:70]6[CH:76]=[C:75]([C:77]7[CH:82]=[CH:81][C:80]([N:83]8[CH2:88][CH2:87][N:86]([CH3:89])[CH2:85][CH2:84]8)=[CH:79][CH:78]=7)[CH2:74][C@@H:71]6[CH:72]=[N:73][C:67]=5[CH:66]=4)=[CH:11][C:12]=2[N:18]=[CH:17]3)=[CH:27][CH:26]=1)=[O:57])=[O:56]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 86717257HCID 86717257, compound

Product 1

HCID 86717256HCID 86717256, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Excess piperidine was added (0.1 mL, 1 mmol) to a solution of PBD 26 (36.4 mg, 0.03 mmol) in DMF (0.9 mL). The mixture was allowed to stir at room temperature for 20 min, at which point the reaction had gone to completion (as monitored by LC/MS). The reaction mixture was diluted with CH2Cl2 (50 mL) and the organic phase was washed with H2O (3×50 mL) until complete piperidine removal. The organic phase was dried over MgSO4, filtered and excess solvent removed by rotary evaporation under reduced pressure to afford crude product 27 which was used as such in the next step. LC/MS 2.20 min (ES+) m/z (relative intensity) 964 ([M+H]+, 5%).

Workup

  1. washthe organic phase was washed with H2O (3×50 mL) until complete piperidine removal
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customexcess solvent removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-a4bb0a9f7e53477b81d3c4e3713c4fb5
Source dataset
uspto-grants-2016_08
Patent number
US09415117B2

Reaction notes

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