2-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acid → HCID 71062164, compound
Reaction equation
ClC1C(C(=O)N(CCCC)CCCC)=NN(C2C=CC(C(=O)NS(C3C=CC4C(=CC=CC=4)C=3)(=O)=O)=CC=2C(O)=O)C=1C.[Cl:44][C:45]1[C:46]([C:79](=[O:89])[N:80]([CH2:85][CH2:86][CH2:87][CH3:88])[CH2:81][CH2:82][CH2:83][CH3:84])=[N:47][N:48]([C:51]2[CH:61]=[CH:60][C:59]([C:62](=[O:78])[NH:63][S:64]([C:67]3[CH:68]=[C:69]4[C:73](=[CH:74][CH:75]=3)[N:72]([CH2:76][CH3:77])[CH2:71][CH2:70]4)(=[O:66])=[O:65])=[CH:58][C:52]=2[C:53]([O:55]CC)=[O:54])[C:49]=1[CH3:50]>>[Cl:44][C:45]1[C:46]([C:79](=[O:89])[N:80]([CH2:85][CH2:86][CH2:87][CH3:88])[CH2:81][CH2:82][CH2:83][CH3:84])=[N:47][N:48]([C:51]2[CH:61]=[CH:60][C:59]([C:62](=[O:78])[NH:63][S:64]([C:67]3[CH:68]=[C:69]4[C:73](=[CH:74][CH:75]=3)[N:72]([CH2:76][CH3:77])[CH2:71][CH2:70]4)(=[O:66])=[O:65])=[CH:58][C:52]=2[C:53]([OH:55])=[O:54])[C:49]=1[CH3:50]Participants
3
Procedure
Following a procedure analogous to that for the synthesis of Intermediate 91F, ethyl 2-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(1-ethylindolin-5-ylsulfonylcarbamoyl)benzoate (180 mg, 0.27 mmol) was converted to the title compound (58 mg, 32%) after purification by preparative HPLC. 1H NMR (DMSO-d6) δ 8.41 (d, J=2.0 Hz, 1H), 8.17 (dd, J=8.3, 2.1 Hz, 1H), 7.69-7.64 (m, 2H), 7.52 (d, J=1.8 Hz, 1H), 6.83 (d, J=8.6 Hz, 1H), 3.54 (t, J=8.6 Hz, 2H), 3.28-3.24 (m, 6H), 3.00 (t, J=8.6 Hz, 2H), 2.10 (s, 3H), 1.57-1.41 (m, 4H), 1.33-1.26 (m, 2H), 1.14-1.08 (m, 5H), 0.91 (t, J=7.4 Hz, 3H), 0.75 (t, J=7.3 Hz, 3H); MS(ESI+) m/z 644.3 (M+H)+.
Sources & evidence
- ORD record
- ord-f72ac501e280481a98db5b7930dd3098
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346795B2
Reaction notes
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