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

HRID 1582144Notes

Reaction equation

Cl[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]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[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]>C1COCC1>[CH:19]1([C:18]2[C:12]3[S:11][C:10]([NH:9][C:7](=[O:8])[C:6]4[CH:27]=[CH:28][C:3]([CH2:2][N:33]([CH2:32][CH2:31][O:30][CH3:29])[CH3:34])=[CH:4][CH:5]=4)=[N:14][C:13]=3[C:15]([O:25][CH3:26])=[CH:16][CH:17]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 0.095 g (0.23 mMol) 4-chloromethyl-N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-benzamide in 1 ml THF were added 0.16 g (1.83 mMol) N-(2-methoxyethyl)-methyl amine. The reaction mixture was heated to 70° C. for 2 h. The solvent was evaporated to dryness, the residue taken up in ethyl acetate and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated to dryness in vacuo. The residue was subjected to column chromatography (dichloro methane/methanol 19:1) to yield (0.087 g (81%) of N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-benzamide as a light yellow foam. ES-MS m/e (%): 468 ([M+H]+, 100).

Workup

customThe solvent was evaporated to dryness
washwashed with water and brine
dry with materialThe organic phase was dried over sodium sulfate
customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-255d532127fd40b497da4919ed54d810
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734179B2

Reaction notes

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