5-Fluoroindole-3-acetic acid → (S)-2-(5-fluoro-1H-indol-3-yl)-N-(2-phenyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl)acetamide

HRID 1506641Notes

Reaction equation

HRID 1506641 reaction equation
FC1C=C(C[C@H](NC(=O)CN2C3CCCCC=3C(C(F)(F)F)=N2)C2N(C3C=CC(OC)=CC=3)C=CN=2)C=C(F)C=1.[C:41]1([CH2:47][C@@H:48]([C:50]2[O:54][N:53]=[C:52]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[N:51]=2)[NH2:49])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[F:61][C:62]1[CH:63]=[C:64]2[C:68](=[CH:69][CH:70]=1)[NH:67][CH:66]=[C:65]2[CH2:71][C:72](O)=[O:73]>>[F:61][C:62]1[CH:63]=[C:64]2[C:68](=[CH:69][CH:70]=1)[NH:67][CH:66]=[C:65]2[CH2:71][C:72]([NH:49][C@H:48]([C:50]1[O:54][N:53]=[C:52]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[N:51]=1)[CH2:47][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:73]

Participants

4

Reactant 3

HCID 967505-Fluoroindole-3-acetic acidHCID 2512349(S)-2-phenyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamineHCID 90281246N-[(1S)-2-(3,5-difluorophenyl)-1-[1-(4-methoxyphenyl)imidazol-2-yl]ethyl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetamide

Product 1

HCID 90281308(S)-2-(5-fluoro-1H-indol-3-yl)-N-(2-phenyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl)acetamide

Procedure

The title compound was prepared according to the method presented for the synthesis of compound 5F of Example 5 utilizing 18A and 2-(5-fluoro-1H-indol-3-yl)acetic acid. 1H NMR (400 MHz, DMSO) δ 10.92 (s, 1H), 8.90 (d, J=8.0 Hz, 1H), 7.94 (m, 2H), 7.68-7.39 (m, 3H), 7.37-7.06 (m, 8H), 6.85 (td, J=9.2, 2.5 Hz, 1H), 5.34 (dd, J=13.8, 9.2 Hz, 1H), 3.46-3.20 (m, 4H); MS (m/z) 441.1 [M+H]+.

Sources & evidence

ORD record
ord-4161806084de433f9ae20d257838069d
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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