Lawesson's reagent → N-Cyclopentyl-1-ethyl-5-(5-isopropyl-1,3,4-thiadiazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

HRID 490916Notes

Reaction equation

HRID 490916 reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([C:13]([NH:15][NH:16][C:17](=O)[CH:18]([CH3:20])[CH3:19])=O)=[CH:11][N:10]=[C:9]3[N:22]([CH2:25][CH3:26])[N:23]=[CH:24][C:8]=23)[CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>C(#N)C>[CH:1]1([NH:6][C:7]2[C:8]3[CH:24]=[N:23][N:22]([CH2:25][CH3:26])[C:9]=3[N:10]=[CH:11][C:12]=2[C:13]2[S:36][C:17]([CH:18]([CH3:20])[CH3:19])=[N:16][N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 576751924-(Cyclopentylamino)-1-ethyl-N'-isobutyryl-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

Product 1

HCID 57675135N-Cyclopentyl-1-ethyl-5-(5-isopropyl-1,3,4-thiadiazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

Intermediate 10 was dissolved in acetonitrile (5 ml) then treated with Lawesson's reagent (0.125 g) and heated under nitrogen at 65° C. for 66 h. Volatiles were removed in vacuo and the residue was purified by mass directed autoprep HPLC to afford Example 6. LCMS showed MH+=357; TRET=3.59 min.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue was purified by mass
  3. customto afford Example 6
  4. customTRET=3.59 min.

Sources & evidence

ORD record
ord-5cbff5b52d93484cb6e1203e63befdbb
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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