2-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acid → HCID 71063074, compound

HRID 528918Notes

Reaction equation

HRID 528918 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.[CH2:44]([N:48]([C:92]1[CH:101]=[CH:100][C:95]([C:96]([O:98]C)=[O:97])=[CH:94][CH:93]=1)[C:49]([C:51]1[C:55]([Cl:56])=[C:54]([CH3:57])[N:53]([C:58]2[CH:63]=[CH:62][C:61]([C:64](=[O:79])[NH:65][S:66]([C:69]3[CH:78]=[CH:77][C:76]4[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=4)[CH:70]=3)(=[O:68])=[O:67])=[CH:60][C:59]=2[C:80]([N:82]2[CH2:91][CH2:90][C:89]3[C:84](=[CH:85][CH:86]=[CH:87][CH:88]=3)[CH2:83]2)=[O:81])[N:52]=1)=[O:50])[CH2:45][CH2:46][CH3:47]>>[CH2:44]([N:48]([C:92]1[CH:93]=[CH:94][C:95]([C:96]([OH:98])=[O:97])=[CH:100][CH:101]=1)[C:49]([C:51]1[C:55]([Cl:56])=[C:54]([CH3:57])[N:53]([C:58]2[CH:63]=[CH:62][C:61]([C:64](=[O:79])[NH:65][S:66]([C:69]3[CH:78]=[CH:77][C:76]4[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=4)[CH:70]=3)(=[O:67])=[O:68])=[CH:60][C:59]=2[C:80]([N:82]2[CH2:91][CH2:90][C:89]3[C:84](=[CH:85][CH:86]=[CH:87][CH:88]=3)[CH2:83]2)=[O:81])[N:52]=1)=[O:50])[CH2:45][CH2:46][CH3:47]

Participants

3

Reactant 2

HCID 710621452-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acidHCID 71063117HCID 71063117, compound

Product 1

HCID 71063074HCID 71063074, compoundYield 124.3%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 91F, methyl 4-(N-butyl-4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazole-3-carboxamido)benzoate (Example 154, 2 mg, 2.0 μmol) was converted to the title compound (2 mg, 94%). 1H NMR (CD3OD, 2:1 mixture of amide rotamers) δ 8.71 (s, 1H), 8.10 (d, J=8.1 Hz, 1H), 8.06 (s, 2H), 8.04-7.97 (m, 2.5H), 7.93 (d, J=2.0 Hz, 0.5H), 7.87 (d, J=8.6 Hz, 1H), 7.75-7.64 (m, 3H), 7.54 (d, J=8.1 Hz, 0.5H), 7.41 (d, J=8.8 Hz, 0.5H), 7.22-7.18 (m, 3.5H), 7.01-6.99 (m, 1.5H), 6.73 (d, J=7.0 Hz, 1H), 4.97 (br s, 1H), 4.69 (br s, 1H), 4.52-4.31 (m, 2H), 4.17 (br s, 1H), 3.93 (br s, 1H), 3.64-3.43 (m, 1H), 2.94-2.78 (m, 1H), 2.21-2.17 (m, 1H), 2.16 (s, 2H), 2.14 (s, 1H), 2.06-2.00 (m, 1H), 1.64-1.56 (m, 1H), 1.44-1.20 (m, 3H), 0.93-0.81 (m, 3H); MS(ESI+) m/z 804.3 (M+H)+.

Sources & evidence

ORD record
ord-4f3e9791de564881bd00ae6c99e7b0ea
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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