(2-Methoxyethyl)(methyl)amine → HCID 22992242, compound

HRID 1168178Notes

Reaction equation

Cl[CH2:2][C:3]([N:5]([CH2:7][C:8]1[CH:33]=[CH:32][C:11]([C:12]([NH:14][C:15]2[S:16][C:17]3[C:23]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:22][CH:21]=[C:20]([O:30][CH3:31])[C:18]=3[N:19]=2)=[O:13])=[CH:10][CH:9]=1)[CH3:6])=[O:4].[CH3:34][O:35][CH2:36][CH2:37][NH:38][CH3:39].C(=O)([O-])O.[Na+]>ClCCl>[CH3:34][O:35][CH2:36][CH2:37][N:38]([CH2:2][C:3]([N:5]([CH2:7][C:8]1[CH:33]=[CH:32][C:11]([C:12]([NH:14][C:15]2[S:16][C:17]3[C:23]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:22][CH:21]=[C:20]([O:30][CH3:31])[C:18]=3[N:19]=2)=[O:13])=[CH:10][CH:9]=1)[CH3:6])=[O:4])[CH3:39]

Participants

Conditions

Temperature: 55 °C

Procedure

4-[(Chloroacetyl-methyl-amino)-methyl]-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-benzamide (100 mg, 205 mmol) are dissolved in N-(2-methoxyethyl)-methylamine (1.8 ml, 21 mmol) and the mixture stirred for 2 h at 55° C. Saturated aqueous sodium hydrogen carbonate is added (50 ml) and dichloromethane (50 ml) are added, the phases are separated and the aqueous phase extracted twice with 50 ml dichloromethane. The combined organic layers are dried with magnesium sulfate and evaporated. Flash chromatography (silica, dichloromethane containing 5% methanol) afforded the title compound as white crystals (74% yield), mp 171-173° C. MS: m/e=542 (M+H+).

Workup

additionare added
customthe phases are separated
extractionthe aqueous phase extracted twice with 50 ml dichloromethane
dry with materialThe combined organic layers are dried with magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-8e37eade5f2e44549aa829b7109153b8
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624163B2

Reaction notes

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