Methylamine → HCID 22722415, compound

HRID 1977972Notes

Reaction equation

HRID 1977972 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)(=[O:36])=[O:35])(=[O:27])=[O:26])[CH:5]=[C:6]([CH:23]=1)[O:7][CH2:8][CH2:9][CH2:10][O:11]C1C=CC=C2C(NC(=O)C=12)=O.C[NH2:45]>O1CCCC1.C(O)C.C(OCC)C>[CH3:1][C:2]1[CH:3]=[C:4]([O:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)(=[O:36])=[O:35])(=[O:27])=[O:26])[CH:5]=[C:6]([CH:23]=1)[O:7][CH2:8][CH2:9][CH2:10][O:11][NH2:45]

Participants

6

Reactant 2

HCID 6329MethylamineHCID 22722670HCID 22722670, compound

Product 1

HCID 22722415HCID 22722415, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture 3-[5-methyl-3-(2-(4-methylpiperazinylsulfonyl)phenylsulfonyloxy)phenoxy]propoxyphthalimide (156 mg, 0.25 mmol), as prepared in the previous step, and 40% aqueous methylamine (1.50 mL, 21.5 mmol) in tetrahydrofuran (5 mL) and ethanol (5 mL) was stirred at room temperature for 4 hours. The solution was concentrated and the residue was purified by flash chromatography (10% methanol in dichloromethane) giving a slurry that was twice dissolved in diethyl ether, filtered, and concentrated giving the title compound as a clear oil (113 mg, 91%). 1H NMR (300 MHz, CDCl3/CD3OD) δ8.22 (dd, 1H, J=7.9, 1.3 Hz), 8.18 (dd, 1H, J=7.9, 1.4 Hz), 7.83 (td, 1H, J=7.7, 1.4 Hz), 7.70 (td, 1H, J=7.7, 1.3 Hz), 6.60 (br s, 1H), 6.56 (br s, 1H), 6.53 (t, 1H, J=2.1 Hz), 3.93 (t, 2H, J=6.3 Hz), 3.80 (t, 2H, J=6.2 Hz), 3.41 (m, 5H), 2.50 (br t, 4H, J=4.9 Hz), 2.30 (s, 3H), 2.24 (s, 3H), 2.00 (pentet, 2H, J=6.2 Hz).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by flash chromatography (10% methanol in dichloromethane)
  3. customgiving a slurry that
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-321a23acb42d41a4994cc088ab8a1454
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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