Ethyl 2-(6-(5-cyano-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate → [6-(5-Aminomethyl-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

HRID 1798301Notes

Reaction equation

HRID 1798301 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[S:19][C:20]([C:23]#[N:24])=[N:21][N:22]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[S:19][C:20]([CH2:23][NH2:24])=[N:21][N:22]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

4

Reactant 1

HCID 67252448Ethyl 2-(6-(5-cyano-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 67253777[6-(5-Aminomethyl-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl esterYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of [6-(5-cyano-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.41 g, 1.14 mmol) in ethanol (10 mL) was added 10% Pd/C (0.036 g, 0.34 mmol) and the suspension was hydrogenated at 50 psi for 3 hours. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to give [6-(5-aminomethyl-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.22 g, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.43 (s, 1H), 8.69 (br. s., 3H), 7.51 (d, J=2.26 Hz, 1H), 7.34 (d, J=1.94 Hz, 1H), 5.58 (dd, J=8.92, 2.55 Hz, 1H), 4.41 (s, 2H), 4.05 (q, J=7.14 Hz, 2H), 3.16 (dd, J=16.72, 1.75 Hz, 1H), 2.35-2.42 (m, 1H), 2.35 (s, 3H), 1.14 (t, J=7.15 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e6fb2b60ec67480c856c837adb54ab27
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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