5-Fluoroindole-3-acetic acid → N-(1-(5-(4-chlorophenyl)oxazol-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-fluoro-1H-indol-3-yl)acetamide

HRID 1506669Notes

Reaction equation

HRID 1506669 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.Cl.[Cl:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[O:53][CH:52]=[N:51][C:50]=2[CH:54]([NH2:64])[CH2:55][C:56]2[CH:61]=[C:60]([F:62])[CH:59]=[C:58]([F:63])[CH:57]=2)=[CH:45][CH:44]=1.[F:65][C:66]1[CH:67]=[C:68]2[C:72](=[CH:73][CH:74]=1)[NH:71][CH:70]=[C:69]2[CH2:75][C:76](O)=[O:77]>>[Cl:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[O:53][CH:52]=[N:51][C:50]=2[CH:54]([NH:64][C:76](=[O:77])[CH2:75][C:69]2[C:68]3[C:72](=[CH:73][CH:74]=[C:66]([F:65])[CH:67]=3)[NH:71][CH:70]=2)[CH2:55][C:56]2[CH:61]=[C:60]([F:62])[CH:59]=[C:58]([F:63])[CH:57]=2)=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 967505-Fluoroindole-3-acetic acidHCID 902801711-(5-(4-Chlorophenyl)oxazol-4-yl)-2-(3,5-difluorophenyl)ethanamine hydrochlorideHCID 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 90281367N-(1-(5-(4-chlorophenyl)oxazol-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-fluoro-1H-indol-3-yl)acetamide

Procedure

The title compound was prepared according to the method presented for the synthesis of compound 5F of Example 5 utilizing 33G and 2-(5-fluoro-1H-indol-3-yl)acetic acid. 1H NMR (400 MHz, DMSO) δ 10.88 (s, 1H), 8.76 (d, J=8.3 Hz, 1H), 8.47 (s, 1H), 7.63 (d, J=7.9 Hz, 2H), 7.43 (d, J=8.0 Hz, 2H), 7.26 (dd, J=8.8, 4.6 Hz, 1H), 7.08 (d, J=12.4 Hz, 2H), 6.91-6.83 (m, 4H), 5.31 (d, J=7.9 Hz, 1H), 3.44 (s, 2H), 3.22-3.11 (m, 1H), 3.06 (dd, J=13.3, 7.0 Hz, 1H). MS (m/z) 510.1 [M+H]+.

Sources & evidence

ORD record
ord-35ffa823e51b482089a54f27381d97ca
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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