4-Carbamoylbenzoic acid → HCID 178457788, compound

HRID 518660Notes

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].[C:43]([C:46]1[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][CH:47]=1)(=[O:45])[NH2:44]>>[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:50](=[O:51])[C:49]2[CH:53]=[CH:54][C:46]([C:43]([NH2:44])=[O:45])=[CH:47][CH:48]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 5060574-Carbamoylbenzoic acid

HCID 178457785HCID 178457785, compound

Product 1

HCID 178457788HCID 178457788, compoundYield 11.9%

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-carbamoylbenzoic acid. The material was purified via preparative HPLC (0.1% NH4OH in ACN/H2O) to provide (E)-N1-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)terephthalamide (11.9% yield). MS m/z=576.2 [M+H], calc 575.71 for C31H41N7O4.

Workup

customThe material was purified via preparative HPLC (0.1% NH4OH in ACN/H2O)

Sources & evidence

ORD record: ord-1258a88560484f99b1a683bd84d3689b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

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