p-(Methylsulphonyl)benzoic acid → HCID 178457819, compound

HRID 518658Notes

Reaction equation

HRID 518658 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](C2C=CC3C=CSC=3C=2)=[O:33])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:43][S:44]([C:47]1[CH:55]=[CH:54][C:50](C(O)=O)=[CH:49][CH:48]=1)(=[O:46])=[O:45]>>[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](=[O:33])[C:50]2[CH:54]=[CH:55][C:47]([S:44]([CH3:43])(=[O:46])=[O:45])=[CH:48][CH:49]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 77670p-(Methylsulphonyl)benzoic acidHCID 178457785HCID 178457785, compound

Product 1

HCID 178457819HCID 178457819, compoundYield 22%

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-(methylsulfonyl)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)-4-(methylsulfonyl)benzamide (22.0% yield). MS m/z=611.4 [M+H], calc 610.77 for C31H42N6O5S.

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-40a8510bd74f448f8350afd97ced900b
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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