(S)-N-(1-(5-bromo-2-((2-(2-methoxyethoxy)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-methoxyethoxy)ethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

HRID 2170338Notes

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:64]([NH:74][C:75](=[O:93])[CH2:76][N:77]2[C:85]3[C:84]([F:87])([F:86])[CH2:83][CH2:82][C:81]([F:89])([F:88])[C:80]=3[C:79]([CH:90]([F:92])[F:91])=[N:78]2)[CH2:65][C:66]2[CH:71]=[C:70]([F:72])[CH:69]=[C:68]([F:73])[CH:67]=2)=[N:52][C:53]([NH:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH3:63])=[N:54][CH:55]=1>>[F:91][CH:90]([F:92])[C:79]1[C:80]2[C:81]([F:89])([F:88])[CH2:82][CH2:83][C:84]([F:86])([F:87])[C:85]=2[N:77]([CH2:76][C:75]([NH:74][C@H:64]([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][O:59][CH2:60][CH2:61][O:62][CH3:63])[N:52]=2)[CH2:65][C:66]2[CH:71]=[C:70]([F:72])[CH:69]=[C:68]([F:73])[CH:67]=2)=[O:93])[N:78]=1

Participants

Reactant 2

HCID 90281318(S)-N-(1-(5-bromo-2-((2-(2-methoxyethoxy)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 90281278(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-methoxyethoxy)ethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

Procedure

The title compound (17B) was prepared according to the method presented for the synthesis of compound 11J of Example 11 utilizing 17A. 1H NMR (400 MHz, CD3OD) δ 8.82 (d, J=8.2 Hz, 1H), 8.06 (s, 1H), 7.52-7.31 (m, 2H), 7.21 (dd, J=10.7, 8.5 Hz, 1H), 7.01-6.56 (m, 2H), 6.44 (d, J=6.0 Hz, 2H), 5.23 (t, J=6.7 Hz, 1H), 5.05 (s, 2H), 3.84-3.63 (m, 6H), 3.57 (m, 2H), 3.37 (s, 3H), 3.17-2.90 (m, 2H), 2.65-2.39 (m, 4H). MS (m/z) 774.58 [M+H]+.

Sources & evidence

ORD record: ord-3753613b65184236b84a44b881e35a01
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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