Pyridine → Morpholine-4-carboxylic acid [4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-amide

HRID 1582169Notes

Reaction equation

HRID 1582169 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.Cl[C:26](OC1C=CC=CC=1)=[O:27].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:26]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[O:27])[S:11][C:7]=2[C:6]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 8083MorpholineHCID 10340Sodium CarbonateHCID 15891Phenyl chloroformateHCID 220157354-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amine

Product 1

HCID 10309328Morpholine-4-carboxylic acid [4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-amideYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-ylamine (265 mg, 1.0 mmol) in dichloromethane (15 ml) is subsequently added pyridine (0.24 ml, 3.0 mmol) and phenyl chloroformate (0.5 ml, 1.2 mmol) and the resulting solution stirred for 45 min at ambient temperature. Then morpholine (313 mg, 3.6 mmol) is added and the mixture stirred at ambient temperature for 15 min and at 40° C. for 2.5 h. After cooling to ambient temperature, saturated aqueous sodium carbonate (15 ml) is added, the organic phase is separated, dried and the solvent evaporated in vacuo. Flash chromatography (silica, eluent: dichloromethane containing methanol (gradient from 0 to 5%)) afforded the title compound as white crystals (21% yield), mp 217-220° C. MS: m/e=378 (M+H+).

Workup

  1. stirringthe mixture stirred at ambient temperature for 15 min and at 40° C. for 2.5 h
  2. temperatureAfter cooling to ambient temperature
  3. customthe organic phase is separated
  4. customdried
  5. customthe solvent evaporated in vacuo
  6. additionFlash chromatography (silica, eluent: dichloromethane containing methanol (gradient from 0 to 5%))

Sources & evidence

ORD record
ord-45a8820e144a4d45bbe41be830ec3696
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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