HCID 66668749, compound → HCID 66664953, compound

HRID 2176434Notes

Reaction equation

HRID 2176434 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:32][C:13]3=[N:14][C:15]([N:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)=[CH:16][C:17](=[O:18])[N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[S:32][C:13]3=[N:14][C:15]([N:19]4[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:23][CH2:24]4)=[CH:16][C:17](=[O:18])[N:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 66668749HCID 66668749, compound

Product 1

HCID 66664953HCID 66664953, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-butyl 4-(2-(3-nitrophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (220, 0.480 mmol, 1.0 equiv) is dissolved in 5 mL methanol. To the solution is added palladium on carbon (51.1 mg). The reaction is stirred under an atmosphere of hydrogen for 3 h. Upon completion, the mixture is filtered through celite and concentrated in vacuo to give crude tert-butyl 4-(2-(3-aminophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.37 (s, 1H), 7.20-7.29 (m, 1H), 7.13 (d, J=7.83 Hz, 1H), 6.83 (dd, J=7.63, 1.76 Hz, 1H), 5.46 (s, 1H), 3.87 (s, 2H), 3.45-3.65 (m, 8H), 1.48 (m, 9H);

Workup

  1. filtrationUpon completion, the mixture is filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-141acc5508dd42d1a74fcf1cb23e142c
Source dataset
uspto-grants-2015_06
Patent number
US09066948B2

Reaction notes

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