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

HRID 1926614Notes

Reaction equation

HRID 1926614 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 70.3%

Conditions

Temperature
60 °C

Procedure

4-cyano-3-(2,4-dichlorophenyl)-5-(methylsulfonyl)thiophene-2-carboxamide (0.026 g, 0.069 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 4-cyano-3-(2,4-dichlorophenyl)-5-[2-(hydroxymethyl)morpholin-4-yl]thiophene-2-carboxamide (0.020 g, 66%) as a white solid. LCMS: (FA) ES+ 412. 1H NMR (400 MHz, d4-methanol) δ: 7.76 (s, 1H), 7.49 (d, 1H), 7.40 (d, 1H), 4.08-3.92 (m, 3H), 3.84-3.72 (m, 2H), 3.69-3.59 (m, 2H), 3.15-3.08 (m, 2H).

Workup

  1. concentrationThe residue was concentrated in vacuo and column chromatography

Sources & evidence

ORD record
ord-efa1c8135c3741e2b27aea042b2ba870
Source dataset
uspto-grants-2012_05
Patent number
US08183240B2

Reaction notes

Loading…