1-Methylpiperazine → HCID 56963635, compound

HRID 931449Notes

Reaction equation

HRID 931449 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:33]=[CH:32][C:21]([C:22]([NH:24][CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[O:23])=[CH:20][CH:19]=3)[O:15][C:16]=2[CH3:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>CS(C)=O>[CH3:17][C:16]1[O:15][C:14]([C:18]2[CH:33]=[CH:32][C:21]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[O:23])=[CH:20][CH:19]=2)=[N:13][C:12]=1[CH2:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:38]2[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 56963634HCID 56963634, compound

Product 1

HCID 56963635HCID 56963635, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of fluoride 48 (112 mg, 0.24 mmol) and 1-methylpiperazine (1 mL) in DMSO (1 mL) was stirred in a sealed tube at 130° C. for 16 h. The solvent was evaporated and the residue was suspended in ice/water (50 mL) for 1 h. The mixture was partitioned between CHCl3 (200 mL) and water (50 mL) and the solvent evaporated. The mixture was dissolved in EtOAc (5 mL) and the precipitated filtered to give benzamide 49 (41 mg, 31%) as a white powder: mp (EtOAc) 210-215° C.; 1H NMR δ 9.23 (s, 1H, CONH), 8.56 (br s, 1H, H-2′), 8.46 (dd, J=4.8, 1.6 Hz, 1H, H-6′), 8.00 (d, J=8.6 Hz, 2H, H-2, H-6), 7.91 (d, J=8.6 Hz, 2H, H-3, H-5), 7.73 (dt, J=8.0, 2.0 Hz, 1H, H-4′), 7.50 (d, J=9.1 Hz, 2H, H-3″, H-5″), 7.36 (ddd, J=7.9, 4.7, 0.6 Hz, 1H, H-5′), 7.02 (d, J=9.1 Hz, 2H, H-2″, H-6″), 4.49-4.53 (m, 4H, CH2SO2, CH2N), 3.30 (br t, J=4.9 Hz, 4H, 2×CH2N), 2.40 (br t, J=4.9 Hz, 4H, 2×CH2N), 2.20 (s, 3H, CH3), 2.12 (s, 3H, CH3); 13C NMR δ 165.5, 157.8, 154.0, 149.6, 148.8, 148.1, 135.3, 135.1, 134.9, 129.7 (2), 128.8, 128.0 (2), 126.4, 125.4 (2), 123.4 (2), 113.3 (2), 54.1 (2), 53.2, 46.4 (2), 45.6, 40.4, 9.6; MS m/z 546.8 (MH+, 100%).

Workup

  1. customThe solvent was evaporated
  2. waitthe residue was suspended in ice/water (50 mL) for 1 h
  3. customThe mixture was partitioned between CHCl3 (200 mL) and water (50 mL)
  4. customthe solvent evaporated
  5. dissolutionThe mixture was dissolved in EtOAc (5 mL)
  6. filtrationthe precipitated filtered

Sources & evidence

ORD record
ord-7e896d6aa5f0464dbdc03ab0f88a6cec
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

Loading…