3-Hydroxyazetidine hydrochloride → (4-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)pyridin-2-yl)(3-hydroxyazetidin-1-yl)methanone

HRID 1052296Notes

Reaction equation

HRID 1052296 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28]([OH:30])=O)[CH:23]=4)[NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Cl.[OH:32][CH:33]1[CH2:36][NH:35][CH2:34]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)[CH2:11][CH2:12][C:13]1[N:14]=[C:15]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:28]([N:35]4[CH2:36][CH:33]([OH:32])[CH2:34]4)=[O:30])[CH:23]=3)[NH:19][C:16]2=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 899635894-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)picolinic acid

Product 1

HCID 73053960(4-(2-(3,5-Dimethoxyphenethyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)pyridin-2-yl)(3-hydroxyazetidin-1-yl)methanone

Procedure

The compound was prepared by using procedure analogous to those described for the synthesis of Example 73, Step 3 starting from 4-{2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazin-6-yl}pyridine-2-carboxylic acid and 3-hydroxyazetidine hydrochloride (from Oakwood). LCMS calculated for C25H26N5O4 (M+H)+: m/z=460.2. Found 460.2.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-95dba04f2ea34d96bf98b02f875695f1
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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