2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetic acid → (S)-5-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)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 2170350Notes

Reaction equation

HRID 2170350 reaction equation
BrC1C([C@H](NC(=O)CN2C3CCCCC=3C(C(F)(F)F)=N2)CC2C=C(F)C=C(F)C=2)=NC(SC)=NC=1.[F:37][CH:38]([F:56])[C:39]1[C:47]2[C:46]([F:49])([F:48])[CH2:45][CH2:44][C:43]([F:51])([F:50])[C:42]=2[N:41]([CH2:52][C:53]([OH:55])=O)[N:40]=1.Cl.[N:58]1([CH2:63][CH2:64][NH:65][C:66]2[N:71]=[C:70]([C@@H:72]([NH2:82])[CH2:73][C:74]3[CH:79]=[C:78]([F:80])[CH:77]=[C:76]([F:81])[CH:75]=3)[C:69]([C:83]3[CH:84]=[CH:85][C:86]([F:92])=[C:87]([CH:91]=3)[C:88]([NH2:90])=[O:89])=[CH:68][N:67]=2)[CH:62]=[CH:61][N:60]=[N:59]1>>[N:58]1([CH2:63][CH2:64][NH:65][C:66]2[N:71]=[C:70]([C@@H:72]([NH:82][C:53](=[O:55])[CH2:52][N:41]3[C:42]4[C:43]([F:50])([F:51])[CH2:44][CH2:45][C:46]([F:49])([F:48])[C:47]=4[C:39]([CH:38]([F:37])[F:56])=[N:40]3)[CH2:73][C:74]3[CH:79]=[C:78]([F:80])[CH:77]=[C:76]([F:81])[CH:75]=3)[C:69]([C:83]3[CH:84]=[CH:85][C:86]([F:92])=[C:87]([CH:91]=3)[C:88]([NH2:90])=[O:89])=[CH:68][N:67]=2)[CH:62]=[CH:61][N:60]=[N:59]1

Participants

4

Reactant 3

HCID 867198242-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetic acidHCID 90281265(R)-N-(1-(5-bromo-2-(methylthio)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamideHCID 90281374(S)-5-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-4-(1-amino-2-(3,5-difluorophenyl)ethyl)pyrimidin-5-yl)-2-fluorobenzamide hydrochloride

Product 1

HCID 90281460(S)-5-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)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 (23F) was prepared according to the method presented for the synthesis of compound 11G of Example 11 utilizing 2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetic acid and 23E. 1H NMR (400 MHz, CD3OD) δ 8.71 (d, J=7.6 Hz, 1H), 8.06 (s, 1H), 7.99 (s, 1H), 7.74 (s, 1H), 7.43-7.25 (m, 2H), 7.20 (dd, J=10.8, 8.5 Hz, 1H), 6.97-6.58 (m, 2H), 6.42 (d, J=6.2 Hz, 2H), 5.32-5.18 (m, 2H), 5.09 (s, 2H), 4.73 (m, 2H), 4.01 (m, 2H), 3.01 (m, 2H), 2.66-2.34 (m, 4H). MS (m/z) 767.06 [M+H]+.

Sources & evidence

ORD record
ord-363683b4213f4a0cbf10473ad4cd4ed1
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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