Hydrochloric Acid → HCID 136252345, compound

HRID 624547Notes

Reaction equation

HRID 624547 reaction equation
[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:7]=3[N:6]=[C:5]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[C:4]=2[CH:3]=1.Cl>CO.[Pd]>[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][C:14]([CH2:16][NH2:17])=[CH:15][C:7]=3[N:6]=[C:5]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136377200HCID 136377200, compound

Product 1

HCID 136252345HCID 136252345, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of 2-Methyl-10-(4-methyl-piperazin-1-yl)-4H-3-thia-4,9-diaza-benzo[f]azulene-7-carbonitrile, prepared as described in the previous step, (0.25 g) in methanol (90 mL) was added concentrated HCl (0.4 mL) and Pd black (57 mg). Hydrogenation was carried out at 50 psi for 1 h. More Pd black (147 mg) was added. The mixture was shaken at 50 psi for 22 h. The catalyst was filtered and washed with methanol. The filtrate was concentrated, treated with saturated sodium bicarbonate solution (5 mL), and concentrated to dryness. The product was purified by silica column. LC-MS: m/z 342 (M+1). 1H NMR (CD3OD, 400 MHz): δ (ppm) 6.89-6.85 (m, 2H), 6.64 (d, 1H), 6.34 (d, 1H), 3.66 (s, 2H), 3.46 (m, 4H), 2.54 (m, 4H), 2.34 (s, 3H), 2.30 (d, 3H).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. additiontreated with saturated sodium bicarbonate solution (5 mL)
  5. concentrationconcentrated to dryness
  6. customThe product was purified by silica column

Sources & evidence

ORD record
ord-0837dbc0021749d79fd1236cf839205e
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

Loading…