Triethylamine → HCID 11562605, compound

HRID 1992522Notes

Reaction equation

HRID 1992522 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][CH2:20][NH2:21])[CH2:14]1.C([N:24](CC)CC)C.[O:29]=[C:30]1[NH:35][C:34]2C=[C:37]([S:40](Cl)(=[O:42])=[O:41])[CH:38]=[CH:39][C:33]=2[S:32][CH2:31]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][CH2:20][NH:21][S:40]([C:37]2[CH:38]=[CH:39][C:33]3[S:32][CH2:31][C:30](=[O:29])[NH:35][C:34]=3[N:24]=2)(=[O:42])=[O:41])[CH2:14]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 218737563-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-sulfonyl chlorideHCID 58955137HCID 58955137, compound

Product 1

HCID 11562605HCID 11562605, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

N1-[1-(6-Methoxy-[1,5]naphthyridin-4-yl)-pyrrolidin-3-yl]-ethane-1,2-diamine (213 mg, 0.74 mmol) (from Example 2c) was dissolved in DCM (2 mL) with triethylamine (0.31 mL, 2.2 mmol) and cooled in an ice bath. The cooled solution was treated with 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-sulfonyl chloride and stirred 45 minutes. The reaction mixture was diluted with chloroform and poured into saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with chloroform, and the combined organic layers were washed with brine, dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 0-10% MeOH in CDCl3 (1% NH4OH) to afford the title compound as a white solid (174 mg, 46%): LC/MS m/z 515 (M+H)+; 1H NMR (CDCl3, 400 MHz) δ 8.28 (d, J=5 Hz, 1H), 8.04 (d, J=9 Hz, 1H), 7.43-7.36 (m, 2H), 6.97 (d, J=9 Hz, 1H), 6.30 (d, J=5 Hz, 1H), 4.03 (m, 1H), 3.94 (s, 3H), 3.85 (m, 1H), 3.71 (m, 1H), 3.43 (s, 2H), 3.38 (m, 1H), 3.06 (m, 2H), 2.82 (m, 2H), 2.10 (m, 1H), 1.85 (m, 1H), 1.70-1.60 (m, 1H).

Workup

  1. temperaturecooled in an ice bath
  2. extractionThe aqueous layer was extracted with chloroform
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica, 0-10% MeOH in CDCl3 (1% NH4OH)

Sources & evidence

ORD record
ord-ac8b9c95c80b49fcb71aa07d36d1acba
Source dataset
uspto-grants-2010_01
Patent number
US07648984B2

Reaction notes

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