Toluene → HCID 16117417, compound

HRID 1005792Notes

Reaction equation

HRID 1005792 reaction equation
Cl[C:2]1[O:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH:20]([CH3:22])[CH3:21])=[C:9]([C:23]([F:26])([F:25])[F:24])[CH:8]=2)[N:6]=1.C(N1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=O)C.[C:36]1(C)C=CC=CC=1>>[CH:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:33]3[CH2:32][CH2:31][CH2:36][CH2:35][CH2:34]3)[O:3][CH:4]=2)=[CH:8][C:9]=1[C:23]([F:26])([F:25])[F:24])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 1140TolueneHCID 837951-AcetylpiperazineHCID 21906818HCID 21906818, compound

Product 1

HCID 16117417HCID 16117417, compound

Procedure

A solution of compound 30 (20 mg, 0.05 mmole) and 1-acetyl piperazine (19.2 mg, 0.15 mmole) in toluene (1.0 ml) was stirred at 100° C. for five hours. Solvent was evaporated and the residue was purified on a 5-g silica gel cartridge eluting with EtOAc. The title compound 26 was obtained as a white solid. 11.2 mg, 45.8%. 1H-NMR (CDCl3, 300 MHz) δ 1.18 (d, J=7.0 Hz, 6H), 2.15(s, 3H), 3.49-3.62 (m, 7H) 3.74 (m, 2H), 6.89 (d, J=8.0 Hz, 1H), 7.15-7.21 (m, 2H), 7.39-7.41 (m, 2H), 7.52 (s, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.96 (s, 1H); MS (APCI) m/z 490(M+H)+.

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified on a 5-g silica gel cartridge
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-b989e9fcb48b41e0a910a3f37bed80a0
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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