(2-Methoxyethyl)(methyl)amine → 4-[4-methoxy-2-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-benzoylamino)-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1582130Notes

Reaction equation

HRID 1582130 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24](=[O:33])[C:25]4[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][CH:26]=4)=[N:19][C:18]=3[C:17]([O:34][CH3:35])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:36][O:37][CH2:38][CH2:39][NH:40][CH3:41]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[S:21][C:20]([NH:23][C:24](=[O:33])[C:25]4[CH:30]=[CH:29][C:28]([CH2:31][N:40]([CH2:39][CH2:38][O:37][CH3:36])[CH3:41])=[CH:27][CH:26]=4)=[N:19][C:18]=3[C:17]([O:34][CH3:35])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 207255084-[2-(4-chloromethyl-benzoylamino)-4-methoxy-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 865888404-[4-methoxy-2-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-benzoylamino)-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.30 g (0.58 mMol) 4-[2-(4-chloromethyl-benzoylamino)-4-methoxy-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester in 10 ml THF were added 0.16 g (1.75 mMol) N-(2-methoxyethyl)-methyl amine. The reaction mixture was heated to 70° C. for 5 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 0.27 g (82%) of 4-[4-methoxy-2-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-benzoylamino)-benzothiazol-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a white foam. ES-MS m/e (%): 567 ([M+H]+, 100).

Workup

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

Sources & evidence

ORD record
ord-ec961ee8dd3d4df9b05dacf3afc14500
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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