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

HRID 1506653Notes

Reaction equation

HRID 1506653 reaction equation
ClC1C=CC(C2[O:9]C(C(NC(=O)CC3C4C(=CC=C(F)C=4)NC=3)CC3C=C(F)C=C(F)C=3)=CN=2)=CC=1.FC(F)(F)[C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[NH:44][CH:43]=[C:42]2[CH2:48][C:49]([OH:51])=O.[Cl:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[C:62]([C@@H:66]([NH2:76])[CH2:67][C:68]3[CH:73]=[C:72]([F:74])[CH:71]=[C:70]([F:75])[CH:69]=3)=[N:63][O:64][CH:65]=2)=[CH:57][CH:56]=1.Cl.ClC1C=CC(C2OC(C(N)CC3C=C(F)C=C(F)C=3)=CN=2)=CC=1>>[Cl:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[C:62]([C@@H:66]([NH:76][C:49](=[O:51])[CH2:48][C:42]3[C:41]4[C:45](=[CH:46][CH:47]=[C:39]([OH:9])[CH:40]=4)[NH:44][CH:43]=3)[CH2:67][C:68]3[CH:73]=[C:72]([F:74])[CH:71]=[C:70]([F:75])[CH:69]=3)=[N:63][O:64][CH:65]=2)=[CH:57][CH:56]=1

Participants

5

Reactant 4

HCID 224907262-(5-Trifluoromethyl-1H-indol-3-YL)acetic acidHCID 902803201-(2-(4-Chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethanamine hydrochlorideHCID 90280390(S)-1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethanamineHCID 90290342N-(1-(2-(4-chlorophenyl)oxazol-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-fluoro-1H-indol-3-yl)acetamide

Product 1

HCID 90281437(S)-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 19F substituting 2-(5-hydroxy-1H-indol-3-yl)acetic acid for 2-(5-(trifluoromethyl)-1H-indol-3-yl)acetic acid and (S)-1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethanamine for 19E to provide the desired compound (26): 1H NMR (400 MHz, DMSO) δ 10.46 (s, 1H), 9.04 (s, 1H), 8.65 (d, 1H), 7.35-7.20 (m, 3H), 7.06 (d, 1H), 6.92 (t, 1H), 6.87 (d, 1H), 6.77 (d, 1H), 6.71 (d, 2H), 6.54 (dd, 1H), 5.25 (q, 1H), 3.39-3.25 (m, 2H), 3.08 (d, 2H); MS (m/z) 508.8 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6e29e25fc4e54a0498ba78a114891667
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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