Dichloromethane → N-[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-morpholin-4-ylmethyl-isonicotinamide

HRID 2222158Notes

Reaction equation

HRID 2222158 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][N:28]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.CO.C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:25][O:24][C:14]1[C:12]2[N:13]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:26]=[CH:27][N:28]=[C:3]([CH2:2][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[CH:4]=3)[S:10][C:11]=2[C:17]([CH:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 10340Sodium CarbonateHCID 227195612-Chloromethyl-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide

Product 1

HCID 11431298N-[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-morpholin-4-ylmethyl-isonicotinamideYield 60%

Reagents, catalysts & solvents 2

HCID 21584013Chloroform ethylacetateSolventHCID 21584188Chloroform methanolSolvent

Procedure

2-Chloromethyl-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide (300 mg, 0.72 mmol) and morpholine (2.1 ml, 25 mmol) are heated to 30° C. for 30 min. The mixture is then cooled to room temperature, treated with dichloromethane (15 ml) and saturated aqueous sodium carbonate (15 ml), the phases are separated and the aqueous layer extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (silica, eluent chloroform/ethyl acetate, then chloroform/methanol) afforded the title compound as white solid (60% yield). MS: m/e=469(M+H+), mp 199-201° C.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous layer extracted twice with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55ef5a647d694982b224351f1cb9a167
Source dataset
uspto-grants-2008_05
Patent number
US07371748B2

Reaction notes

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