1,3-DI-Boc-2-methylisothiourea → HCID 178432665, compound

HRID 2388000Notes

Reaction equation

HRID 2388000 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][C:10]2([CH3:17])[CH3:16])=[CH:4][N:3]=1.[C:18]([O:22][C:23]([NH:25][C:26](=[N:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])SC)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl.[Hg](Cl)Cl>[CH3:1][C:2]1[C:7]([NH:8]/[C:26](/[NH:29][C:30](=[O:31])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[N:25]/[C:23](=[O:24])[O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:6][C:5]([CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][C:10]2([CH3:17])[CH3:16])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 5466031,3-DI-Boc-2-methylisothioureaHCID 59405032HCID 59405032, compound

Product 1

HCID 178432665HCID 178432665, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-5-(1,3,3-trimethylpiperidin-4-yl)pyridine-3-amine (0.814 g, 3.49 mmol) in DCM (50 mL) were added 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (1.52 g, 5.23 mmol), mercury (II) chloride (1.42 g, 5.23 mmol) and TEA (2.92 mL, 20.9 mmol). The reaction mixture was allowed to stir overnight at rt then filtered through a Celite® pad and washed with DCM. The filtrate was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give di-tert-butyl ((Z)-{[2-methyl-5-(1,3,3-trimethylpiperidin-4-yl)pyridine-3-yl]amino}methylylidene)biscarbamate (0.79 g, 48%) as a white solid. LCMS (FAL): Rt=5.08 min, m/z=476.6 (M+H).

Workup

  1. filtrationthen filtered through a Celite® pad
  2. washwashed with DCM
  3. washThe filtrate was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a58d4629a83949929616407b257f9013
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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