tert-Butyl 4-carbamothioylpiperidine-1-carboxylate → HCID 57929940, compound

HRID 1929989Notes

Reaction equation

HRID 1929989 reaction equation
Br[CH:2]([C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1)[C:3]([C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=1[F:13])=O.[NH2:26][C:27]([CH:29]1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1)=[S:28]>CN(C=O)C>[CH:23]([C:20]1[N:18]2[N:19]=[C:14]([C:2]3[S:28][C:27]([CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[N:26][C:3]=3[C:5]3[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=3[F:13])[CH:15]=[CH:16][C:17]2=[N:22][N:21]=1)([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 57929989HCID 57929989, compound

Product 1

HCID 57929940HCID 57929940, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2,4,5-trifluorophenyl)ethanone (0.90 g, 2.2 mmol; prepared using General Procedure J from Preparation #F.1 and Preparation #G.1, General Procedure K with H2SO4, and General Procedure A.2), tert-butyl 4-(aminocarbothioyl)tetrahydropyridine-1-(2H)-carboxylate (Maybridge, 0.8 g, 3.3 mmol) and DMF (20 mL) was stirred at ambient temperature for about 24 h. The reaction was quenched with saturated aqueous NaHCO3 and extracted with Et2O (300 mL). The organic layer was dried over Na2SO4, decanted, and concentrated. The crude material was loaded onto a silica gel column and eluted with a gradient of 0-10% MeOH in DCM to give the title compound (0.41 g, 34%): LC/MS (Table 1, Method a) Rt=4.18 min; MS m/z: 559.3 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with Et2O (300 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated
  6. washeluted with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-00c5691150fc4f658097c088978f0450
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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