HCID 71062246, compound → HCID 70692162, compound

HRID 528814Notes

Reaction equation

ClC1C(C(=O)N(CCCC)CCCC)=NN(C2C=CC(C(NS(C3C=C4C(C=CC(C(O)=O)=C4)=CC=3)(=O)=O)=O)=CC=2C(N2CCC3C(=CC=CC=3)C2)=O)C=1C.[Cl:56][C:57]1[C:58]([C:109](=[O:119])[N:110]([CH2:115][CH2:116][CH2:117][CH3:118])[CH2:111][CH2:112][CH2:113][CH3:114])=[N:59][N:60]([C:63]2[CH:96]=[CH:95][C:66]([C:67]([NH:69][S:70]([C:73]3[CH:82]=[C:81]4[C:76]([CH:77]=[CH:78][CH:79]=[C:80]4[O:83][CH2:84][C:85]4[CH:94]=[CH:93][C:88]([C:89]([O:91]C)=[O:90])=[CH:87][CH:86]=4)=[CH:75][CH:74]=3)(=[O:72])=[O:71])=[O:68])=[CH:65][C:64]=2[C:97]([N:99]2[CH2:108][CH2:107][C:106]3[C:101](=[CH:102][CH:103]=[CH:104][CH:105]=3)[CH2:100]2)=[O:98])[C:61]=1[CH3:62]>>[Cl:56][C:57]1[C:58]([C:109](=[O:119])[N:110]([CH2:115][CH2:116][CH2:117][CH3:118])[CH2:111][CH2:112][CH2:113][CH3:114])=[N:59][N:60]([C:63]2[CH:96]=[CH:95][C:66]([C:67]([NH:69][S:70]([C:73]3[CH:82]=[C:81]4[C:76]([CH:77]=[CH:78][CH:79]=[C:80]4[O:83][CH2:84][C:85]4[CH:86]=[CH:87][C:88]([C:89]([OH:91])=[O:90])=[CH:93][CH:94]=4)=[CH:75][CH:74]=3)(=[O:71])=[O:72])=[O:68])=[CH:65][C:64]=2[C:97]([N:99]2[CH2:108][CH2:107][C:106]3[C:101](=[CH:102][CH:103]=[CH:104][CH:105]=3)[CH2:100]2)=[O:98])[C:61]=1[CH3:62]

Participants

Reactant 2

HCID 71062246HCID 71062246, compound

HCID 86718880HCID 86718880, compound

Product 1

HCID 70692162HCID 70692162, compoundYield 51%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 46A, methyl 4-((7-(N-(4-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoyl)sulfamoyl)naphthalen-1-yloxy) methyl)benzoate (Example 26, 10 mg, 0.011 mmol) was converted to the title compound (5 mg, 49%). 1H NMR (CD3OD, 2:1 mixture of amide rotamers) δ 9.17 (d, J=1.8 Hz, 1H), 8.24-8.00 (m, 6H), 7.81-7.56 (m, 5H), 7.35-7.03 (m, 4.5H), 6.89-6.87 (m, 0.5H), 5.48 (s, 2H), 4.56 (br s, 2H), 3.77-3.42 (m, 4H), 3.24-3.14 (m, 1H), 3.06 (br s, 1H), 2.89 (br s, 2H), 2.37 (s, 2H), 2.32 (s, 1H), 1.63-1.20 (m, 6H), 1.21-1.03 (m, 2H), 1.01-0.88 (m, 3H), 0.86-0.63 (m, 3H); MS(ESI+) m/z 890.4 (M+H)+.

Sources & evidence

ORD record: ord-03ac79af493a4e78967a76227edf82ae
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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