Acetonitrile → HCID 70009098, compound

HRID 1266038Notes

Reaction equation

HRID 1266038 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[C:14]2[NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1.[CH3:22]C#N>[Pd](Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6]/[C:7](/[CH3:22])=[CH:8]/[C:9]1[C:14]2[NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 20577072HCID 20577072, compound

Product 1

HCID 70009098HCID 70009098, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
75 °C

Procedure

Palladium chloride (0.418 mmol, 0.074 g) was added to a solution of 6-(5-Oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-9-yl)-hex-5-ynoic acid methyl ester (8.36 mmol, 2.39 g) in 50 mL CH3CN. The reaction mixture was heated at 70-80° C. for 2.5 h. The solvent was removed and the residue was purified by flash silica gel chromatography eluting with a gradient of 0-5% MeOH in EtOAc to give 2.11 g (88%) of a yellow solid: mp=175-176° C.; 1H NMR (DMSO-d6) δ 1.86-1.98 (m, 2H), 2.43 (t, 2H, J=6.0 Hz), 2.75 (t, 2H, J=6.0 Hz), 3.52-3.54 (m, 2H), 3.57 (s, 3H), 4.21 (br s, 2H), 6.34 (s, 1H), 7.07 (t, 1H, J=6.0 Hz), 7.65 (d, 1H, J=6.0 Hz), 7.75 (d, 1H, J=6.0 Hz), 8.23 (t, 1H, J=6.0 Hz); HRMS calcd. for C16H18N2O3 (M+) 286.1317, found (M+) 286.1310; Anal. C16H18N2O3.0.25H2O) C, H, N.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash silica gel chromatography
  3. washeluting with a gradient of 0-5% MeOH in EtOAc

Sources & evidence

ORD record
ord-f7af723301d442e8af1a1463d4bbd0c4
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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