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

HRID 1892199Notes

Reaction equation

HRID 1892199 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>[C:33]([O:32][C:30](=[O:31])[NH:29]/[C:26](/[NH:8][C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][C:10]2([CH3:17])[CH3:16])[CH:6]=1)=[N:25]\[C:23](=[O:24])[O:22][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:36])([CH3:34])[CH3:35]

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-bc0b929de7db4eb9a44a691569899221
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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