Hydrochloric Acid → HCID 25230951, compound

HRID 2272941Notes

Reaction equation

HRID 2272941 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]2[N:10]=[C:11]([C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[O:21])[C:12]3[S:17][C:16]([CH:18]=[CH2:19])=[CH:15][C:13]=3[N:14]=2)[CH:2]=1.Cl>C(O)C.[Pd]>[CH2:18]([C:16]1[S:17][C:12]2[C:11]([C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[O:21])=[N:10][C:9]([NH:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[N:14][C:13]=2[CH:15]=1)[CH3:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25230950HCID 25230950, compound

Product 1

HCID 25230951HCID 25230951, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of Example 10 (0.025 g, 0.066 mmol) in ethanol (5 ml) was treated with palladium/activated carbon (10%, 0.0025 g) and HCl (1.25M in MeOH, 0.19 mmol). The Flask was thoroughly evacuated and placed under 1 atmosphere of hydrogen gas. The mixture was stirred under hydrogen overnight at room temperature, evacuated and filtered through celite. The filtrate was reduced in vacuo to give the title compound as a yellow solid in 70% yield, >95% purity. LC-MS m/z=381.0 [M+H]+; RT=3.19; LC-MS method 1. 1H NMR: δH (400 MHz, D6-DMSO) 1.33 (3H, t, J 7.5 Hz), 2.95 (2H, q, J 7.5 Hz), 4.71 (2H, b), 7.08 (1H, s), 7.28-7.35 (2H, m), 7.78 (1H, d, J 8.0 Hz), 8.06 (1H, bt), 8.17 (1H, d, J 4.5 Hz), 8.43 (1H, d, J 4.5 Hz), 8.63 (1H, bd), 8.40-8.65 (1H, b).

Workup

  1. customThe Flask was thoroughly evacuated
  2. customevacuated
  3. filtrationfiltered through celite

Sources & evidence

ORD record
ord-95f523bb03044bc0afc6c62d98c03fc9
Source dataset
uspto-grants-2015_09
Patent number
US09120807B2

Reaction notes

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