(S)-N-(1-(5-bromo-2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)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-oxa-6-azaspiro[3.3]heptan-6-yl)pyrimidin-5-yl)-2-fluorobenzamide

HRID 2170334Notes

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:63]([NH:73][C:74](=[O:92])[CH2:75][N:76]2[C:84]3[C:83]([F:86])([F:85])[CH2:82][CH2:81][C:80]([F:88])([F:87])[C:79]=3[C:78]([CH:89]([F:91])[F:90])=[N:77]2)[CH2:64][C:65]2[CH:70]=[C:69]([F:71])[CH:68]=[C:67]([F:72])[CH:66]=2)=[N:52][C:53]([N:56]2[CH2:62][C:58]3([CH2:61][O:60][CH2:59]3)[CH2:57]2)=[N:54][CH:55]=1>>[F:90][CH:89]([F:91])[C:78]1[C:79]2[C:80]([F:88])([F:87])[CH2:81][CH2:82][C:83]([F:86])([F:85])[C:84]=2[N:76]([CH2:75][C:74]([NH:73][C@H:63]([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]([N:56]3[CH2:57][C:58]4([CH2:61][O:60][CH2:59]4)[CH2:62]3)[N:52]=2)[CH2:64][C:65]2[CH:70]=[C:69]([F:71])[CH:68]=[C:67]([F:72])[CH:66]=2)=[O:92])[N:77]=1

Participants

Reactant 2

HCID 90281573(S)-N-(1-(5-bromo-2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)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 90281380(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-oxa-6-azaspiro[3.3]heptan-6-yl)pyrimidin-5-yl)-2-fluorobenzamide

Procedure

The title compound (15B) was prepared according to the method presented for the synthesis of compound 11J of Example 11 utilizing 15A. 1H NMR (400 MHz, CD3OD) δ 8.69 (d, J=8.0 Hz, 1H), 8.09 (s, 1H), 7.45-7.31 (m, 2H), 7.21 (dd, J=10.7, 8.6 Hz, 1H), 7.03-6.63 (m, 2H), 6.42 (d, J=6.1 Hz, 2H), 5.23 (dd, J=15.1, 7.6 Hz, 1H), 5.05 (s, 2H), 4.88 (s, 4H), 4.39 (q, J=9.9 Hz, 4H), 3.00 (m, 2H), 2.50 (m, 4H). MS (m/z) 754.24 [M+H]+.

Sources & evidence

ORD record: ord-d9c2fedcdddc4aa682ea561ac370a195
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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