Triethylamine → (S)-N-[5-(4-Methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-4-morpholinobenzenesulfonamide

HRID 433906Notes

Reaction equation

HRID 433906 reaction equation
[NH2:1][C@H:2]1[CH2:7][C:6]2[C:8]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.C(N(CC)CC)C.[N:26]1([C:32]2[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(Cl)Cl>[CH3:18][N:15]1[CH2:14][CH2:13][N:12]([C:8]2[C:6]3[CH2:7][C@H:2]([NH:1][S:38]([C:35]4[CH:34]=[CH:33][C:32]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[CH:37][CH:36]=4)(=[O:39])=[O:40])[CH2:3][O:4][C:5]=3[CH:11]=[CH:10][CH:9]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11139461(S)-3-amino-5-(4-methylpiperazin-1-yl)-1,4-dihydro-2H-1-benzopyranHCID 149512114-(Morpholin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 69210902(S)-N-[5-(4-Methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-4-morpholinobenzenesulfonamideYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-amino-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (120 mg, 0.485 mmol) in anhydrous methylene chloride (10 mL) were added triethylamine (81 μL, 0.582 mmol) and 4-(4-morpholinyl)benzenesulfonyl chloride (140 mg, 0.534 mmol; described in: Galliani, G. Eur. Pat. Appl. EP 335,758, 1989, Chem. Abstr. 1990, 112, 98374d [125393-22-8]). The reaction mixture was stirred at room temperature for 4 h, washed with a 2 M NH3 solution, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica (eluent: chloroform/ethanol, 90:10+0.5% conc. NH3) affording 141 mg (61% yield) of the title compound as a white solid: mp sinters >100° C.; [α]22D+10° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 472 (56, M+).

Workup

  1. washwashed with a 2 M NH3 solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography on silica (eluent: chloroform/ethanol, 90:10+0.5% conc. NH3)

Sources & evidence

ORD record
ord-bc9ec2c0d4a34dc0b642dfad57dc9324
Source dataset
uspto-grants-2003_12
Patent number
US06670359B2

Reaction notes

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