HCID 59549043, compound → HCID 68505622, compound

HRID 39048Notes

Reaction equation

HRID 39048 reaction equation
C1(C2C3C=CC4C(=O)NCCC=CCCNC(=O)CN(C=3C=4)C=2C2C=CC(OCC3C=C([N+]([O-])=O)C=CC=3N3CCN(S(C)(=O)=O)CC3)=CC=2)CCCCC1.[CH2:56]([NH:60][C:61]([C:63]1[CH:71]=[C:70]2[C:66]([C:67]([CH:110]3[CH2:115][CH2:114][CH2:113][CH2:112][CH2:111]3)=[C:68]([C:80]3[CH:85]=[CH:84][C:83]([O:86][CH2:87][C:88]4[CH:93]=[C:92]([N:94]5[CH2:98][CH2:97][CH2:96][C:95]5=[O:99])[CH:91]=[CH:90][C:89]=4[N:100]4[CH2:105][CH2:104][N:103]([S:106]([CH3:109])(=[O:108])=[O:107])[CH2:102][CH2:101]4)=[CH:82][CH:81]=3)[N:69]2[CH2:72][C:73](=[O:79])[NH:74][CH2:75][CH2:76]C=C)=[CH:65][CH:64]=1)=[O:62])[CH2:57][CH:58]=[CH2:59]>>[CH:110]1([C:67]2[C:66]3[CH:65]=[CH:64][C:63]4[C:61](=[O:62])[NH:60][CH2:56][CH2:57][CH:58]=[CH:59][CH2:76][CH2:75][NH:74][C:73](=[O:79])[CH2:72][N:69]([C:70]=3[CH:71]=4)[C:68]=2[C:80]2[CH:81]=[CH:82][C:83]([O:86][CH2:87][C:88]3[CH:93]=[C:92]([N:94]4[CH2:98][CH2:97][CH2:96][C:95]4=[O:99])[CH:91]=[CH:90][C:89]=3[N:100]3[CH2:101][CH2:102][N:103]([S:106]([CH3:109])(=[O:107])=[O:108])[CH2:104][CH2:105]3)=[CH:84][CH:85]=2)[CH2:111][CH2:112][CH2:113][CH2:114][CH2:115]1

Participants

3

Reactant 2

HCID 59549043HCID 59549043, compoundHCID 74928751HCID 74928751, compound

Product 1

HCID 68505622HCID 68505622, compoundYield 32%

Procedure

The target product 17-cyclohexyl-18-[4-[2-(4-methanesulfonyl-piperazin-1-yl)-5-(2-oxo-pyrrolidin-1-yl)-benzyloxy]-phenyl]-1,4,11-triaza-tricyclo[11.5.2.016,19]icosa-7,13(20),14,16(19),17-pentaene-3,12-dione 12 was synthesized in 32% yield, following the procedure reported for the synthesis of compound 3 and using intermediate 11-7 instead of intermediate 3-11; m/z=808 (M+H)+. NMR (DMSO-d6): δ (ppm) 1.21-1.27 (m, 4H, cyclohexyl), 1.66-1.94 (m, 6H, cyclohexyl), 2.06 (qt, J=7.6 Hz, 2H, CH2 pyrrolidinone), 2.30 (m, 4H, 2×CH2CH═CH), 2.48 (m, 2H, CH2 pyrrolidinone), 2.60 (m, 1H, CH cyclohexyl), 2.92 (s, 3H, SO2CH3), 2.99 (m, 4H, piperidine), 3.28 (m, 4H, piperidine), 3.36 (m, 2H, CH2NHCO), 3.43 (m, 2H, CH2NHCO), 3.82 (t, J=7.1 Hz, 2H, CH2 pyrrolidinone), 4.39 (s, 2H, CH2CONH), 5.23 (s, 2H, CH2O), 5.37 (m, 1H, CH═CH), 5.46 (m, 1H, CH═CH), 7.21 (d, J=8.7 Hz, 2H), 7.26 (d, J=8.7 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.47 (d, J=8.6 Hz, 2H), 7.58 (dd, J=2.6 Hz, 8.7 Hz, 1H), 7.67 (s, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.86 (d, J=2.6 Hz, 1H), 8.27 (m, 1H, NH), 8.46 (broad t, J=5.9 Hz, NH).

Sources & evidence

ORD record
ord-92f1733a7c0b4ea9b500a153960200a3
Source dataset
uspto-grants-2013_09
Patent number
US08524716B2

Reaction notes

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