HCID 71062246, compound → HCID 71062470, compound

HRID 528939Notes

Reaction equation

HRID 528939 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.[CH2:56]([N:60]([CH2:109][C:110]1[CH:115]=[CH:114][C:113]([Cl:116])=[C:112]([Cl:117])[CH:111]=1)[C:61]([C:63]1[C:67]([Cl:68])=[C:66]([CH3:69])[N:65]([C:70]2[CH:96]=[CH:95][C:73]([C:74]([NH:76][S:77]([C:80]3[CH:89]=[C:88]4[C:83]([CH:84]=[CH:85][C:86]([C:90]([O:92]CC)=[O:91])=[CH:87]4)=[CH:82][CH:81]=3)(=[O:79])=[O:78])=[O:75])=[CH:72][C:71]=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])[N:64]=1)=[O:62])[CH2:57][CH2:58][CH3:59]>>[CH2:56]([N:60]([CH2:109][C:110]1[CH:115]=[CH:114][C:113]([Cl:116])=[C:112]([Cl:117])[CH:111]=1)[C:61]([C:63]1[C:67]([Cl:68])=[C:66]([CH3:69])[N:65]([C:70]2[CH:96]=[CH:95][C:73]([C:74]([NH:76][S:77]([C:80]3[CH:89]=[C:88]4[C:83]([CH:84]=[CH:85][C:86]([C:90]([OH:92])=[O:91])=[CH:87]4)=[CH:82][CH:81]=3)(=[O:79])=[O:78])=[O:75])=[CH:72][C:71]=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])[N:64]=1)=[O:62])[CH2:57][CH2:58][CH3:59]

Participants

3

Reactant 2

HCID 71062246HCID 71062246, compoundHCID 86718906HCID 86718906, compound

Product 1

HCID 71062470HCID 71062470, compoundYield 83%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 46A, ethyl 7-(N-(4-(3-(butyl(3,4-dichlorobenzyl)carbamoyl)-4-chloro-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoyl)sulfamoyl)-2-naphthoate (91 mg, 0.10 mmol) was converted to the title compound (73 mg, 83%). 1H NMR (DMSO-d6, mixture of amide rotamers) δ 8.49 (s, 0.5H), 8.45 (s, 0.5H), 8.38 (s, 0.5H), 8.09 (dd, J=11.9, 8.4 Hz, 1.5H), 8.01-7.79 (m, 3H), 7.60-7.41 (m, 2H), 7.29-6.92 (m, 3.5H), 6.81 (d, J=8.4 Hz, 0.5H), 4.80-4.16 (m, 3H), 3.68-2.91 (m, 10.5H), 2.81-2.60 (m, 2H), 2.39-2.30 (m, 0.5H), 2.21-2.06 (m, 3H), 1.42-1.06 (m, 3H), 1.01-0.88 (m, 1.5H), 0.86-0.76 (m, 1H), 0.71-0.50 (m, 1.5H); MS(ESI+) m/z 803.4 (M+H)+.

Sources & evidence

ORD record
ord-73d3e999848a405e9d8d41220e6c763c
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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