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

HRID 2170332Notes

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:61]([NH:71][C:72](=[O:90])[CH2:73][N:74]2[C:82]3[C:81]([F:84])([F:83])[CH2:80][CH2:79][C:78]([F:86])([F:85])[C:77]=3[C:76]([CH:87]([F:89])[F:88])=[N:75]2)[CH2:62][C:63]2[CH:68]=[C:67]([F:69])[CH:66]=[C:65]([F:70])[CH:64]=2)=[N:52][C:53]([NH:56][CH2:57][CH:58]2[CH2:60][CH2:59]2)=[N:54][CH:55]=1>>[CH:58]1([CH2:57][NH:56][C:53]2[N:52]=[C:51]([C@@H:61]([NH:71][C:72](=[O:90])[CH2:73][N:74]3[C:82]4[C:81]([F:83])([F:84])[CH2:80][CH2:79][C:78]([F:85])([F:86])[C:77]=4[C:76]([CH:87]([F:89])[F:88])=[N:75]3)[CH2:62][C:63]3[CH:64]=[C:65]([F:70])[CH:66]=[C:67]([F:69])[CH:68]=3)[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]=2)[CH2:59][CH2:60]1

Participants

Reactant 2

HCID 90281571(S)-N-(1-(5-bromo-2-((cyclopropylmethyl)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 90281382(S)-5-(2-((cyclopropylmethyl)amino)-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)pyrimidin-5-yl)-2-fluorobenzamide

Procedure

The title compound (13B) was prepared according to the method presented for the synthesis of compound 11J of Example 11 utilizing 13A. 1H NMR (400 MHz, CD3OD) δ 8.50 (d, J=7.7 Hz, 1H), 7.73 (s, 1H), 7.24-7.02 (m, 2H), 6.90 (dd, J=10.7, 8.6 Hz, 1H), 6.65-6.24 (m, 2H), 6.13 (d, J=6.1 Hz, 2H), 4.91 (m, 1H), 4.83-4.62 (m, 2H), 3.09 (m, 2H), 2.71 (ddd, J=20.2, 13.3, 7.4 Hz, 2H), 2.37-2.06 (m, 4H), 0.88 (m, 1H), 0.47-0.16 (m, 2H), 0.02 (q, J=5.1 Hz, 2H). MS (m/z) 726.30 [M+H]+.

Sources & evidence

ORD record: ord-e22593f056de492ab7df3c97ad202e12
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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