2-(5-Trifluoromethyl-1H-indol-3-YL)acetic acid → N-[(1S)-1-[4-(4-chlorophenyl)isoxazol-3-yl]-2-(3,5-difluorophenyl)ethyl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetamide

HRID 1506654Notes

Reaction equation

HRID 1506654 reaction equation
ClC1C=CC(C2[O:9][C:10]([CH:13]([NH:23]C(=O)CC3C4C(=CC=C(F)C=4)NC=3)CC3C=C(F)C=C(F)C=3)=CN=2)=CC=1.[F:37][C:38]([F:53])([F:52])C1C=C2C(=CC=1)NC=C2CC(O)=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.Cl[C:79]1[CH:84]=[CH:83][C:82]([C:85]2OC(C(N)CC3C=C(F)C=C(F)C=3)=C[N:89]=2)=[CH:81][CH:80]=1>>[Cl:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[C:62]([C@@H:66]([NH:76][C:10](=[O:9])[CH2:13][N:23]3[C:81]4[CH2:80][CH2:79][CH2:84][CH2:83][C:82]=4[C:85]([C:38]([F:53])([F:52])[F:37])=[N:89]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 90281456N-[(1S)-1-[4-(4-chlorophenyl)isoxazol-3-yl]-2-(3,5-difluorophenyl)ethyl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetamide

Procedure

The title compound was prepared according to the method presented in the synthesis of 19F substituting 2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-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 (27): 1H NMR (400 MHz, DMSO) δ 9.10 (s, 1H), 8.99 (d, 1H), 7.41 (d, 2H), 7.35 (d, 2H), 6.98 (d, 1H), 6.80 (d, 2H), 5.36 (d, 1H), 4.58 (s, 2H), 3.12 (dt, 2H), 2.46 (dd, 2H), 2.22 (d, 2H), 1.61 (s, 4H); MS (m/z) 566.3 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-4669237767c841efbd21bb0f84b9c000
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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