(S)-N-(1-(5-bromo-2-((2-(2-oxoimidazolidin-1-yl)ethyl)amino)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide → (S)-5-(4-(1-(2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)-2-((2-(2-oxoimidazolidin-1-yl)ethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

HRID 2170345Notes

Reaction equation

FC1C=C(C[C@H](C2C([C:34]3[CH:35]=[CH:36][C:37]([F:43])=[C:38]([CH:42]=3)[C:39]([NH2:41])=[O:40])=CN=C(NCCOC)N=2)NC(=O)CN2C3CCCCC=3C(C(F)(F)F)=N2)C=C(F)C=1.Br[C:50]1[C:51]([C@@H:65]([NH:75][C:76](=[O:94])[CH2:77][N:78]2[C:86]3[C:85]([F:88])([F:87])[CH2:84][CH2:83][C:82]([F:90])([F:89])[C:81]=3[C:80]([CH:91]([F:93])[F:92])=[N:79]2)[CH2:66][C:67]2[CH:72]=[C:71]([F:73])[CH:70]=[C:69]([F:74])[CH:68]=2)=[N:52][C:53]([NH:56][CH2:57][CH2:58][N:59]2[CH2:63][CH2:62][NH:61][C:60]2=[O:64])=[N:54][CH:55]=1>>[F:93][CH:91]([F:92])[C:80]1[C:81]2[C:82]([F:89])([F:90])[CH2:83][CH2:84][C:85]([F:88])([F:87])[C:86]=2[N:78]([CH2:77][C:76]([NH:75][C@H:65]([C:51]2[C:50]([C:34]3[CH:35]=[CH:36][C:37]([F:43])=[C:38]([CH:42]=3)[C:39]([NH2:41])=[O:40])=[CH:55][N:54]=[C:53]([NH:56][CH2:57][CH2:58][N:59]3[CH2:63][CH2:62][NH:61][C:60]3=[O:64])[N:52]=2)[CH2:66][C:67]2[CH:68]=[C:69]([F:74])[CH:70]=[C:71]([F:73])[CH:72]=2)=[O:94])[N:79]=1

Participants

Reactant 2

HCID 90281487(S)-N-(1-(5-bromo-2-((2-(2-oxoimidazolidin-1-yl)ethyl)amino)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

HCID 90290144(R)-5-(4-(2-(3,5-difluorophenyl)-1-(2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)ethyl)-2-((2-methoxyethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

Product 1

HCID 90281172(S)-5-(4-(1-(2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)-2-((2-(2-oxoimidazolidin-1-yl)ethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

Procedure

The title compound (22B) was prepared according to the method presented for the synthesis of compound 11J of Example 11 utilizing 22A. 1H NMR (400 MHz, CD3OD) δ 8.88 (m, 1H), 8.07 (s, 1H), 7.47-7.29 (m, 2H), 7.27-7.14 (m, 1H), 6.96-6.59 (m, 2H), 6.45 (d, J=6.4 Hz, 2H), 5.26 (m, 1H), 5.09 (s, 2H), 3.82-3.49 (m, 6H), 3.40 (m, 2H), 3.15-2.95 (m, 2H), 2.51 (m, 4H). MS (m/z) 784.22 [M+H]+.

Sources & evidence

ORD record: ord-288984e1d790463a8ec10fa7422c0d66
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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