3-(Trifluoromethoxy)benzoic acid → HCID 178457789, compound

HRID 518659Notes

Reaction equation

HRID 518659 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:32]([C:34]2[CH:35]=[CH:36][C:37]3C=CS[C:38]=3[CH:42]=2)=[O:33])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[F:43][C:44]([F:56])([F:55])[O:45]C1C=C(C=CC=1)C(O)=O>>[CH:1]([NH:4][C:5]([C@@H:7]1[CH2:8][CH2:9][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:32](=[O:33])[C:34]2[CH:35]=[CH:36][CH:37]=[C:38]([O:45][C:44]([F:56])([F:55])[F:43])[CH:42]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 660963-(Trifluoromethoxy)benzoic acidHCID 178457785HCID 178457785, compound

Product 1

HCID 178457789HCID 178457789, compoundYield 50.3%

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 3-(trifluoromethoxy)benzoic acid. The material was purified via preparative HPLC (0.1% NH4OH in ACN/H2O) to provide (E)-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)-3-(trifluoromethoxy)benzamide (50.3% yield). MS m/z=617.4 [M+H], calc 616.67 for C31H39F3N6O4. 1H NMR (CDCl3) δ ppm: 12.32 (br. s., 1H), 8.30-8.43 (m, 2H), 8.10 (d, J=0.8 Hz, 1H), 7.28-7.31 (m, 1H), 7.01 (s, 1H), 5.34 (d, J=1.0 Hz, 1H), 4.77-4.91 (m, 1H), 4.45-4.55 (m, 2H), 4.14-4.29 (m, 1H), 2.46-2.95 (m, 8H), 2.20-2.27 (m, 2H), 1.73-1.89 (m, 4H), 1.58-1.73 (m, 5H), 1.41-1.57 (m, 3H), 1.22 (d, J=6.6 Hz, 6H).

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-f323bae8b4a448d6810922cae8e172d5
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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