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

Participants

Role	Name	HCID	Charge
Reactant	2-(5-Trifluoromethyl-1H-indol-3-YL)acetic acid	HCID 22490726	—
Reactant	N-[(1S)-2-(3,5-difluorophenyl)-1-[1-(4-methoxyphenyl)imidazol-2-yl]ethyl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetamide	HCID 90281246	—
Reactant	(S)-2-(3,5-difluorophenyl)-1-(1-(4-methoxyphenyl)-1H-imidazol-2-yl)ethanamine	HCID 90281432	—
Reactant	(R)-1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethanamine	HCID 90290315	—
Product	(R)-N-(1-(4-(4-chlorophenyl)isoxazol-3-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-hydroxy-1H-indol-3-yl)acetamide	HCID 90281414	—

Reaction Steps

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]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09220710B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-cc7f84c48f204c9da4c6ac89f6fb3358
Source note	uspto-grants-2015_12