Morpholin-2-ylmethanol → 4-Cyano-3-(2,4-dichlorophenyl)-5-[2-(hydroxymethyl)morpholin-4-yl]thiophene-2-carboxamide

HRID 572634Notes

Reaction equation

HRID 572634 reaction equation
[C:1]([C:3]1[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[C:5]([C:12]([NH2:14])=[O:13])[S:6][C:7]=1S(C)(=O)=O)#[N:2].[OH:23][CH2:24][CH:25]1[O:30][CH2:29][CH2:28][NH:27][CH2:26]1>>[C:1]([C:3]1[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[C:5]([C:12]([NH2:14])=[O:13])[S:6][C:7]=1[N:27]1[CH2:28][CH2:29][O:30][CH:25]([CH2:24][OH:23])[CH2:26]1)#[N:2]

Participants

3

Reactant 2

HCID 3497988Morpholin-2-ylmethanolHCID 580228604-Cyano-3-(2,4-dichlorophenyl)-5-(methylsulfonyl)thiophene-2-carboxamide

Product 1

HCID 441374124-Cyano-3-(2,4-dichlorophenyl)-5-[2-(hydroxymethyl)morpholin-4-yl]thiophene-2-carboxamideYield 70.1%

Conditions

Temperature
60 °C

Procedure

4-cyano-3-(2,4-dichlorophenyl)-5-(methylsulfonyl)thiophene-2-carboxamide (0.013 g, 0.0346 mmol) was dissolved in 2-hydroxymethylmorpholine (0.300 g, 2.56 mmol) and the solution was heated at 60° C. overnight. The residue was concentrated in vacuo and column chromatography was performed and yielded the title compound 87 (0.010 g, 66%) as a white solid. LCMS: (FA) ES+ 412, 414, 416. 1H NMR (400 MHz, d4-methanol) δ: 7.68 (s, 1H), 7.50 (d, 1H), 7.40 (d, 1H), 4.08-3.92 (m, 3H), 3.88-3.56 (m, 4H), 3.16-3.04 (m, 2H).

Workup

  1. concentrationThe residue was concentrated in vacuo and column chromatography

Sources & evidence

ORD record
ord-04eece298cbd40c09e2f9b145f6b179d
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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