5-Hydroxyindoleacetic Acid → N-(1-(2-(4-chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-hydroxy-1H-indol-3-yl)acetamide

HRID 1506649Notes

Reaction equation

HRID 1506649 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:50][C:51]([CH:54]([NH2:64])[CH2:55][C:56]3[CH:61]=[C:60]([F:62])[CH:59]=[C:58]([F:63])[CH:57]=3)=[CH:52][N:53]=2)=[CH:45][CH:44]=1.[OH: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:50][C:51]([CH:54]([NH:64][C:76](=[O:77])[CH2:75][C:69]3[C:68]4[C:72](=[CH:73][CH:74]=[C:66]([OH:65])[CH:67]=4)[NH:71][CH:70]=3)[CH2:55][C:56]3[CH:61]=[C:60]([F:62])[CH:59]=[C:58]([F:63])[CH:57]=3)=[CH:52][N:53]=2)=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 18265-Hydroxyindoleacetic AcidHCID 902803201-(2-(4-Chlorophenyl)oxazol-5-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 90281408N-(1-(2-(4-chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-hydroxy-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 19E and 2-(5-hydroxy-1H-indol-3-yl)acetic acid. 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.81 (d, J=8.3 Hz, 2H), 7.41 (d, J=8.5 Hz, 2H), 7.27 (m, 1H), 7.08 (s, 1H), 6.87-6.76 (m, 2H), 6.60 (m, 1H), 6.47 (d, J=6.0 Hz, 2H), 6.30 (s, 1H), 5.26 (d, J=7.9 Hz, 1H), 3.67 (s, 2H), 3.08-2.93 (m, 2H). MS (m/z) 508.1 [M+H]+.

Sources & evidence

ORD record
ord-0e0aff2b193a45aea9c75e775c5da3c3
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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