Hydrochloric Acid → HCID 12093794, compound

HRID 1838457Notes

Reaction equation

HRID 1838457 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25](=[O:26])[C:24]3[N:23]([C:27]4[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=4)[C:30]#[N:31])[CH:22]=[N:21][C:20]=3[N:19]([CH2:35][CH2:36][CH3:37])[C:18]2=[O:38])=[CH:13][CH:12]=1)(=[O:4])=[O:3].Cl>[Pd].CO>[NH2:31][CH2:30][C:29]1[CH:28]=[C:27]([N:23]2[C:24]3[C:25](=[O:26])[N:17]([C:14]4[CH:13]=[CH:12][C:11]([C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[S:2]([CH3:1])(=[O:4])=[O:3])=[CH:16][CH:15]=4)[C:18](=[O:38])[N:19]([CH2:35][CH2:36][CH3:37])[C:20]=3[N:21]=[CH:22]2)[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12093793HCID 12093793, compound

Product 1

HCID 12093794HCID 12093794, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A Parr bomb was charged with 9 (100 mg, 0.19 mmol), MeOH (10 mL), 1 N HCl (0.2 mL), and catalytic amount of 10% Pd/C. The reaction mixture was exposed to H2 at 38 psi. After 12 h, the reaction was filtered through a pad of Celite® and concentrated in vacuo. The residue was dissolved in CH2Cl2 (10 mL), washed with NaOH (5.0 mL, 30% aqueous), dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography of the residue on silica (8% MeOH/CH2Cl2) provided free base 10 (35 mg, 35%) as a pale yellow solid: ESI-MS m/z: [C28H27N5O4S+H]+ 530; 1H NMR (300 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.12 (d, J=7.5 Hz, 1H), 7.82-7.35 (m, 10H), 4.06 (br t, 2H), 3.80 (s, 2H), 2.79 (s, 3H), 1.83-1.75 (m, 2H), 0.97 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationthe reaction was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (10 mL)
  4. washwashed with NaOH (5.0 mL, 30% aqueous)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49855e942e014d47b4e295c9c314d987
Source dataset
uspto-grants-2004_01
Patent number
US06673810B2

Reaction notes

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