3-Chlorobenzoic Acid → HCID 178457786, compound

HRID 518657Notes

Reaction equation

HRID 518657 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].[Cl:43]C1C=C(C=CC=1)C(O)=O>>[Cl:43][C:38]1[CH:42]=[C:34]([CH:35]=[CH:36][CH:37]=1)[C:32](/[N:31]=[C:14]1/[N:13]([C@H:10]2[CH2:11][CH2:12][C@@H:7]([C:5](=[O:6])[NH:4][CH:1]([CH3:3])[CH3:2])[CH2:8][CH2:9]2)[C:21]2[CH:20]=[C:19]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:18]=[CH:17][C:16]=2[NH:15]/1)=[O:33]

Participants

3

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 178457785HCID 178457785, compound

Product 1

HCID 178457786HCID 178457786, compoundYield 37.4%

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-chlorobenzoic acid. The material was purified via preparative HPLC (0.1% NH4OH in ACN/H2O) to provide (E)-3-chloro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide (37.4% yield). MS m/z=567.4 [M+H], calc 567.12 for C30H39ClN6O3.

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-eaa49ce24f5b4b1aa0c515917e80432b
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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