Triethylamine → HCID 68153929, compound

HRID 341086Notes

Reaction equation

HRID 341086 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:27](=[O:28])[C:11]2=[CH:12][N:13]([CH2:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]2=[N:9]1.C(N(CC)CC)C.[CH3:36][N:37]=[C:38]=[O:39]>ClCCl.O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:27](=[O:28])[C:11]2=[CH:12][N:13]([CH2:20][CH:21]3[CH2:22][CH2:23][N:24]([C:38]([NH:37][CH3:36])=[O:39])[CH2:25][CH2:26]3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]2=[N:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 68153831HCID 68153831, compound

Product 1

HCID 68153929HCID 68153929, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Fluorophenyl)-5-(piperidin-4-ylmethyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (30 mg, 0.080 mmol) was dissolved in dichloromethane (2 ml) and tetrahydrofuran (1 ml), treated with triethylamine (0.011 ml, 0.080 mmol, 1 equiv) and methylimino(oxo)methane (4.55 mg, 0.080 mmol) were added. After 10 minutes, the mixture was concentrated in vacuo and the residue was purified by silica gel gradient chromatography (80:20 to 70:30; dichlormethane:methanol), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 8.85 (1H, s), 8.21 (1H, dd, J=, 7.9, 1.6 Hz), 7.98 (1H, d, J=8.7 Hz), 7.61-7.56 (2H, m), 7.47-7.30 (4H, m), 6.37 (1H, q, J=4.2 Hz), 5.70 (2H, br s), 4.35 (2H, d, J=6.8 Hz), 3.94 (2H, br d, J=13.6 Hz), 2.52 (3H, d, J=4.9 Hz), 2.13-2.02 (1H, m), 1.49 (2H, br d, J=12.3 Hz), 1.25-1.13 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 434.1998 [(M+H)+; calculated for C24H25FN5O2: 434.1987].

Workup

  1. additionwere added
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe residue was purified by silica gel gradient chromatography (80:20 to 70:30; dichlormethane:methanol)

Sources & evidence

ORD record
ord-09f6af536390420f91c460a8add45ac6
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

Loading…