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

HRID 2170336Notes

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

Participants

Reactant 2

HCID 90281488(S)-N-(1-(5-bromo-2-((2-(dimethylamino)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 90281258(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-(dimethylamino)ethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

Procedure

The title compound (16B) was prepared according to the method presented for the synthesis of compound 11J of Example 11 utilizing 16A. 1H NMR (400 MHz, —CD3OD) δ 8.75 (d, J=7.4 Hz, 1H), 8.13 (s, 1H), 7.38 (m, 2H), 7.21 (dd, J=10.8, 8.4 Hz, 1H), 6.98-6.63 (m, 2H), 6.42 (m, 2H), 5.23 (d, J=7.6 Hz, 1H), 5.02 (q, J=16.8 Hz, 2H), 3.88 (m, 2H), 3.45 (t, J=5.5 Hz, 2H), 3.15-2.93 (m, 8H), 2.52 (m, 4H). MS (m/z) 743.60 [M+H]+.

Sources & evidence

ORD record: ord-b020b1a2ff1146daa4b866e6b2775ffc
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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