2-(5-Trifluoromethyl-1H-indol-3-YL)acetic acid → (R)-N-(1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-hydroxy-1H-indol-3-yl)acetamide

HRID 1506655Notes

Reaction equation

HRID 1506655 reaction equation
FC1C=C(C[C@H](NC(=O)CN2C3CCCCC=3C(C(F)(F)F)=N2)C2N(C3C=CC([O:22]C)=CC=3)C=CN=2)C=C(F)C=1.FC(F)(F)[C:43]1[CH:44]=[C:45]2[C:49](=[CH:50][CH:51]=1)[NH:48][CH:47]=[C:46]2[CH2:52][C:53]([OH:55])=O.[Cl:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]2[C:66]([C@H:70]([NH2:80])[CH2:71][C:72]3[CH:77]=[C:76]([F:78])[CH:75]=[C:74]([F:79])[CH:73]=3)=[N:67][O:68][CH:69]=2)=[CH:61][CH:60]=1.FC1C=C(C[C@@H](C2N(C3C=CC(OC)=CC=3)C=CN=2)N)C=C(F)C=1>>[Cl:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]2[C:66]([C@H:70]([NH:80][C:53](=[O:55])[CH2:52][C:46]3[C:45]4[C:49](=[CH:50][CH:51]=[C:43]([OH:22])[CH:44]=4)[NH:48][CH:47]=3)[CH2:71][C:72]3[CH:77]=[C:76]([F:78])[CH:75]=[C:74]([F:79])[CH:73]=3)=[N:67][O:68][CH:69]=2)=[CH:61][CH:60]=1

Participants

5

Reactant 4

HCID 224907262-(5-Trifluoromethyl-1H-indol-3-YL)acetic acidHCID 90281246N-[(1S)-2-(3,5-difluorophenyl)-1-[1-(4-methoxyphenyl)imidazol-2-yl]ethyl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetamideHCID 90281432(S)-2-(3,5-difluorophenyl)-1-(1-(4-methoxyphenyl)-1H-imidazol-2-yl)ethanamineHCID 90290315(R)-1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethanamine

Product 1

HCID 90281414(R)-N-(1-(4-(4-chlorophenyl)isoxazol-3-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 in the synthesis of 5F substituting 2-(5-hydroxy-1H-indol-3-yl)acetic acid for 2-(5-(trifluoromethyl)-1H-indol-3-yl)acetic acid and 28A for 5E to provide the desired compound (28B): 1H NMR (400 MHz, DMSO) δ 10.46 (s, 1H), 9.04 (s, 1H), 8.65 (d, 1H), 7.32-7.20 (m, 3H), 7.06 (d, 1H), 6.95-6.83 (m, 2H), 6.74 (dd, 3H), 6.54 (dd, 1H), 5.25 (q, 1H), 3.41-3.25 (m, 2H), 3.08 (d, 2H); MS (m/z) 509.1 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-cc7f84c48f204c9da4c6ac89f6fb3358
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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