4-Fluoro-3-(trifluoromethyl)benzoic acid → HCID 178457817, compound

HRID 518652Notes

Reaction equation

HRID 518652 reaction equation
[CH:1]([NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:21]3[CH:20]=[C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[N:18]=[CH:17][C:16]=3[NH:15]/[C:14]/2=[N:31]\C(C2C=CC3C=CSC=3C=2)=O)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[F:43][C:44]1[CH:52]=[CH:51][C:47]([C:48]([OH:50])=O)=[CH:46][C:45]=1[C:53]([F:56])([F:55])[F:54]>>[F:43][C:44]1[CH:52]=[CH:51][C:47]([C:48](/[N:31]=[C:14]2/[N:13]([C@H:10]3[CH2:9][CH2:8][C@@H:7]([C:5](=[O:6])[NH:4][CH:1]([CH3:2])[CH3:3])[CH2:12][CH2:11]3)[C:21]3[CH:20]=[C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[N:18]=[CH:17][C:16]=3[NH:15]/2)=[O:50])=[CH:46][C:45]=1[C:53]([F:56])([F:55])[F:54]

Participants

3

Reactant 2

HCID 5222684-Fluoro-3-(trifluoromethyl)benzoic acidHCID 178457785HCID 178457785, compound

Product 1

HCID 178457817HCID 178457817, compoundYield 43.8%

Procedure

The title compound was prepared using a method analogous to the preparation of (E)-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzo[b]thiophene-6-carboxamide, using 4-fluoro-3-(trifluoromethyl)benzoic acid. The material was purified via preparative HPLC (0.1% NH4OH in ACN/H2O) to provide (E)-4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)-3-(trifluoromethyl)benzamide (43.8% yield). MS m/z=619.4 [M+H], calc 618.67 for C31H38F4N6O3.

Workup

  1. customThe title compound was prepared
  2. customThe material was purified via preparative HPLC (0.1% NH4OH in ACN/H2O)

Sources & evidence

ORD record
ord-51005804448f4f32b73306fa160fc809
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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