Dimethylformamide → HCID 57929986, compound

HRID 1929990Notes

Reaction equation

HRID 1929990 reaction equation
Br[CH:2]([C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[N:20][N:21]=2)[N:18]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=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>C([O-])([O-])=O.[Na+].[Na+]>[C:22]([C:19]1[N:17]2[N:18]=[C:13]([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]=[CH:9][C:8]([F:11])=[CH:7][C:6]=3[F:12])[CH:14]=[CH:15][C:16]2=[N:21][N:20]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 57929976HCID 57929976, compound

Product 1

HCID 57929986HCID 57929986, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 2-bromo-2-(3-tert-butyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2,4-difluorophenyl)ethanone (3.78 g, 9.24 mmol; prepared using General Procedure A.2 from Preparation #K.1.1), tert-butyl 4-(aminocarbothioyl)tetrahydropyridine-1-(2H)-carboxylate (3.08 g, 12.6 mmol, Maybridge) and DMF (60 mL) was stirred at ambient temperature for about 2 d. The reaction was diluted with saturated aqueous Na2CO3 and extracted with Et2O (2×200 mL). The organic layers were combined, dried over Na2SO4 and concentrated. The crude material was loaded onto a silica gel column and eluted with a gradient of 30-100% EtOAc in heptane to give the title compound (3.5 g, 68%): LC/MS (Table 1, Method a) Rt=2.64 min; MS m/z: 555.4 (M+H)+.

Workup

  1. extractionextracted with Et2O (2×200 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. washeluted with a gradient of 30-100% EtOAc in heptane

Sources & evidence

ORD record
ord-5cf459e9566440f692f00c3e49c58c4d
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

Loading…