Dimethyl Sulfoxide → 4-({8-[(2-Hydroxyethyl)(methyl)amino]octanoyl}amino)benzamide

HRID 1675683Notes

Reaction equation

[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][CH:18]=1)=[O:15].CS(C)=O>C(#N)C>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][CH:18]=1)=[O:15]

Participants

Conditions

Temperature: 25 °C

Procedure

2-(Methylamino)ethanol (9.5 g, 7 equivalents) is added to a stirred mixture of 4-[(8-bromooctanoyl)amino]benzamide (5.76 g, 16.9 mmol, e.g. which can be as prepared in Intermediate 53 (first or alternative preparation thereof)) and dimethyl sulfoxide (30 mL). The mixture is stirred at 25° C. until the reaction is substantially complete and is then diluted with acetonitrile (115 mL). After stirring for 1 hour the mixture is filtered, washed with ethyl acetate (15 mL) and tert-butyl methyl ether (TBME, 15 mL) before being dried in vacuo to yield the title compound, generally as a solid.

Workup

customalternative preparation
stirringAfter stirring for 1 hour the mixture
filtrationis filtered
washwashed with ethyl acetate (15 mL) and tert-butyl methyl ether (TBME, 15 mL)
custombefore being dried in vacuo

Sources & evidence

ORD record: ord-13bd9bb19ab14daca8a75112533aa18b
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003663B2

Reaction notes

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