(2-Methoxyethyl)(methyl)amine → 4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide dihydrochloride

HRID 51866

Reaction equation

HRID 51866 reaction equation
[Cl:1][CH2:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([N:19]([CH2:21][CH2:22][O:23][CH3:24])[CH3:20])=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:29][O:30][CH2:31][CH2:32][NH:33][CH3:34]>>[ClH:1].[ClH:1].[CH3:29][O:30][CH2:31][CH2:32][N:33]([CH2:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([N:19]([CH2:21][CH2:22][O:23][CH3:24])[CH3:20])=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)=[O:8])=[CH:5][CH:4]=1)[CH3:34]

Participants

3

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 102164874-chloromethyl-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide

Product 1

HCID 227369864-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide dihydrochlorideYield 168%

Procedure

A mixture of 100 mg (0.24 mmol) 4-chloromethyl-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide and 212 mg (2.38 mmol) N-(2-methoxyethyl)methylamine was ultrasonicated at room temperature for 30 minutes. The reaction mixture was then concentrated it vactio and the residue purified by flash chromatography (ethyl acetate). The product-containing fractions were concentrated in vactio and the residue stirred with HCl in ether and ethyl acetate. The resulting crystals were collected by filtration and washed with ether to afford 110 mg (91%) 4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide dihydrochloride as a white crystalline solid. ES-MS m/e (%): 473 (M+H+, 100).

Workup

  1. customwas ultrasonicated at room temperature for 30 minutes
  2. concentrationThe reaction mixture was then concentrated it vactio
  3. customthe residue purified by flash chromatography (ethyl acetate)
  4. concentrationThe product-containing fractions were concentrated in vactio
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-4b691e70949b484ca5d054d9b9c392dd
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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