Ethyl 2-(4-Ethylpiperazin-1-yl)-2-(4-(4-methyl-6-(2-methyl-3-(5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2-carboxamido)phenyl)-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)acetate → 2-(4-Ethylpiperazin-1-yl)-2-(4-(4-methyl-6-(2-methyl-3-(5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2-carboxamido)phenyl)-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)acetic Acid

HRID 1363518Notes

Reaction equation

HRID 1363518 reaction equation
C(C1C=CC(C(NC2C(C)=C(C3N=C(NC4C=CC(C(N(C(C)C)C)C(O)=O)=CC=4)C(=O)N(C)C=3)C=CC=2)=O)=CC=1)(C)(C)C.[CH2:45]([N:47]1[CH2:52][CH2:51][N:50]([CH:53]([C:59]2[CH:64]=[CH:63][C:62]([NH:65][C:66]3[C:71](=[O:72])[N:70]([CH3:73])[CH:69]=[C:68]([C:74]4[CH:79]=[CH:78][CH:77]=[C:76]([NH:80][C:81]([C:83]5[S:87][C:86]6[CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][C:85]=6[CH:84]=5)=[O:82])[C:75]=4[CH3:93])[N:67]=3)=[CH:61][CH:60]=2)[C:54]([O:56]CC)=[O:55])[CH2:49][CH2:48]1)[CH3:46]>>[CH2:45]([N:47]1[CH2:52][CH2:51][N:50]([CH:53]([C:59]2[CH:60]=[CH:61][C:62]([NH:65][C:66]3[C:71](=[O:72])[N:70]([CH3:73])[CH:69]=[C:68]([C:74]4[CH:79]=[CH:78][CH:77]=[C:76]([NH:80][C:81]([C:83]5[S:87][C:86]6[CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][C:85]=6[CH:84]=5)=[O:82])[C:75]=4[CH3:93])[N:67]=3)=[CH:63][CH:64]=2)[C:54]([OH:56])=[O:55])[CH2:49][CH2:48]1)[CH3:46]

Participants

3

Reactant 2

HCID 57625121Ethyl 2-(4-Ethylpiperazin-1-yl)-2-(4-(4-methyl-6-(2-methyl-3-(5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2-carboxamido)phenyl)-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)acetateHCID 576251502-(4-{6-[3-(4-tert-Butylbenzamido)-2-methylphenyl]-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino}phenyl)-2-[isopropyl(methyl)amino]acetic Acid

Product 1

HCID 576251442-(4-Ethylpiperazin-1-yl)-2-(4-(4-methyl-6-(2-methyl-3-(5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2-carboxamido)phenyl)-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)acetic AcidYield 97%

Procedure

Using the same procedure as described for the preparation of 29, saponification of 45 (1.29 g) gave a 97% yield (1.20 g) of 46 as an off-white solid: mp 168-170° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.79 (s, 1H), 9.25 (s, 1H), 7.96 (d, 2H, J=7.5 Hz), 7.70 (s, 1H), 7.29 (m, 6H), 3.86 (m, 1H), 3.71 (s, 3H), 3.37 (q, 2H, J=7.2 Hz), 2.81 (m, 2H), 2.69 (m, 2H), 2.42 (br s, 8H), 2.19 (s, 3H), 1.83 (br s, 2H), 1.61 (br s, 4H), 0.95 (t, 3H, J=7.2 Hz); MS (ESI+) m/z 655 (M+H).

Sources & evidence

ORD record
ord-e2aa56c9dbc34e1bb7973bf96ebaab14
Source dataset
uspto-grants-2011_02
Patent number
US07884108B2

Reaction notes

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